Reaction SMILES: [CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([N+:12]([O-])=O)[CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:15]>[Pd].CO>[NH2:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[C:3](=[O:15])[N:2]([CH3:1])[CH2:11][CH2:10]2
Reactant: CN1CCc2cccc([N+](=O)[O-])c2C1=O
Agent: [Pd]
Solvent: CO
Product: CN1CCc2cccc(N)c2C1=O
Temperature: 25 °C
Reaction time: 18 h
Yield: 88.2 %

Procedure:
A mixture of 1-tent-butoxy-N,N,N′,N′-tetramethylmethanediamine (300 mL, 1452.80 mmol) and 2-methyl-6-nitrobenzonitrile (75 g, 462.55 mmol) was heated at 100° C. for 4 hours. The mixture was evaporated and the residue stirred vigorously in isohexane (1500 mL) for 2 hours. The mixture was filtered and the residue washed with isohexane (2×500 mL) and then air-dried to afford (E)-2-(2-(dimethylamino)vinyl)-6-nitrobenzonitrile (96 g, 95% yield); 1H NMR spectrum (300 MHz, CDCl3): δ 2.98 (6H, s), 5.52 (1H, d), 7.11 (1H, d), 7.40 (1H, t), 7.60-7.70 (2H, m); Mass spectrum: m/z (ESI+) (M+H)+=218.50. b) Methylamine hydrochloride (131 g, 1933.49 mmol) was added to a suspension of (E)-2-(2-(dimethylamino)vinyl)-6-nitrobenzonitrile (84 g, 386.70 mmol) in MeOH (840 mL) and water (840 mL). The mixture was heated at 50° C. for 17 hours and then allowed to cool to room temperature. The mixture was poured into water (1000 mL), stirred for 30 minutes and then filtered. The solid was air-dried to afford (E)-2-(2-(methylamino)vinyl)-6-nitrobenzonitrile (71.1 g, 90% yield) which was used in the next step without further purification; 1H NMR spectrum (300 MHz, DMSO): δ 2.74 (3H, d), 5.41 (1H, d), 6.93-7.03 (1H, m), 7.50-7.70 (3H, m), 7.96-8.01 (1H, m). c) Sulfuric acid (26.2 ml, 492.13 mmol) was added in one portion to a stirred solution of (E)-2-(2-(methylamino)vinyl)-6-nitrobenzonitrile (50 g, 246.07 mmol) and sodium triacetoxyborohydride (78 g, 369.10 mmol) in DME (1000 mL) cooled to −10° C. The mixture was stirred at −10° C. for 10 minutes and then allowed to warm to room temperature and stirred for a further 20 minutes. The mixture was poured into water (1000 mL), basified to ˜pH 10 with a 2N solution of NaOH and then extracted with EtOAc (3×750 mL). The combined organics were dried over MgSO4 and then evaporated to afford 2-methyl-8-nitro-3,4-dihydroisoquinolin-1(2H)-imine (45.5 g) which was used in the next stage without further purification. d) The following step was carried out in 9 separate batches. 2-Methyl-8-nitro-3,4-dihydroisoquinolin-1(2H)-imine (5 g, 24.36 mmol) and Montmorillonite K10 clay (2.5 g) were suspended in a mixture of water (20 mL) and acetonitrile (30 mL). The mixture was heated at 150° C. for 90 minutes in a microwave reactor and then allowed to cool to room temperature. The separate batches were combined and the mixture was then filtered and evaporated. The residue was purified by chromatography on silica, eluting with a gradient of 0-100% EtOAc in isohexane. Fractions containing product were combined and evaporated to afford 2-methyl-8-nitro-3,4-dihydroisoquinolin-1(2H)-one (23.00 g, 51% yield); 1H NMR spectrum (300 MHz, DMSO): δ 3.00-3.08 (5H, m), 3.60 (2H, t), 7.53-7.67 (3H, m); Mass spectrum: m/z (ES+) (M+H)+=207.58. e) A mixture of 2-methyl-8-nitro-3,4-dihydroisoquinolin-1(2H)-one (23 g, 111.54 mmol) and 5% palladium on carbon (4.6 g, 1.08 mmol) in MeOH (230 mL) was stirred under an atmosphere of hydrogen at 5 atm and 25° C. for 18 hours. The mixture was filtered through Dicalite™ and the filtrate was evaporated. The residue was purified by chromatography on silica, eluting with a gradient of 0-100% EtOAc in isohexane. Fractions containing product were combined and evaporated to afford 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (17.33 g, 88% yield); 1H NMR spectrum (300 MHz, DMSO): δ 2.80 (2H, t), 2.96 (3H, s), 3.43 (2H, t), 6.26-6.32 (1H, m), 6.50-6.55 (1H, m), 6.84 (2H, s), 7.00-7.06 (1H, m); Mass spectrum m/z (ES+) (M+H)+=177.44.