Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH3:1][C:2]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]2[N:16]=[N:17][N:18]=[C:8]2[C:7]=1[N+:19]([O-])=O)([CH3:4])[CH3:3]>[Pt].C(O)C>[CH3:4][C:2]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]2[N:16]=[N:17][N:18]=[C:8]2[C:7]=1[NH2:19])([CH3:1])[CH3:3]
Reactant: CC(C)(C)Nc1c([N+](=O)[O-])c2nnnn2c2ccccc12
Agent: [Pt]
Solvent: CCO
Product: CC(C)(C)Nc1c(N)c2nnnn2c2ccccc12

Procedure:
N-(1,1-dimethylethyl)-4-nitrotetrazolo[1,5-a]quinolin-5-amine (4.2 g, Example 18), ethanol (100 mL) and Pt/C (0.5 g) were placed in a Paar apparatus. The mixture was hydrogenated. The reaction mixture was filtered to remove catalyst then concentrated to dryness under vacuum. The residue was recrystallized from ethyl acetate/dichloromethane to provide N5 -(1,1-dimethylethyl)tetrazolo[1,5-a]quinoline-4,5-diamine as a pale blue crystalline solid.
Reaction SMILES: [C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=O)[CH:10]2[O:14][CH2:15][C:16]([O:19][CH3:20])([O:17][CH3:18])[CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21]C([O-])(C)C.[K+].C(OCC)C>C1COCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[CH2:21])[CH:10]2[O:14][CH2:15][C:16]([O:17][CH3:18])([O:19][CH3:20])[CH:9]12)=[O:7])([CH3:2])([CH3:3])[CH3:4]
Reactant: CC(C)(C)[O-]
Reactant: COC1(OC)COC2C(=O)CN(C(=O)OC(C)(C)C)C21
Agent: C[P+](c1ccccc1)(c1ccccc1)c1ccccc1
Agent: [Br-]
Agent: [K+]
Solvent: CCOCC
Solvent: C1CCOC1
Product: C=C1CN(C(=O)OC(C)(C)C)C2C1OCC2(OC)OC
Temperature: 0 °C
Yield: 47.9 %

Procedure:
The keto compound 1e (1.10 g, 3.83 mmol) was dissolved in dry THF (30 mL) and the solution was cooled to 0° C. A solution of methyl triphenylphosphonium bromide (4.0 g, 11.2 mmol) and KOtBu (1.17 g, 10.5 mmol) in dry THF (40 mL) was added in 3 aliquots with 2 hours interval. After 6 hrs the solution was poured into a separatory funnel with diethyl ether (70 mL) and extracted with 10% citric acid (aq)(2*40 mL). The organic phase was washed with saturated aqueous NaHCO3 (40 mL), dried with Na2SO4, filtered and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (heptane: ethyl acetate 4:1) which gave the title compound (524 mg, 48%)
Reaction SMILES: O1CCOCC1.[OH-].[Na+].[CH:9]([N:12]([C:24]1[CH:29]=[CH:28][C:27]2[O:30][CH2:31][O:32][C:26]=2[CH:25]=1)[C:13]([NH:15]C(=O)C1C=CC=CC=1)=[S:14])([CH3:11])[CH3:10]>O>[CH:9]([N:12]([C:24]1[CH:29]=[CH:28][C:27]2[O:30][CH2:31][O:32][C:26]=2[CH:25]=1)[C:13]([NH2:15])=[S:14])([CH3:11])[CH3:10]
Reactant: CC(C)N(C(=S)NC(=O)c1ccccc1)c1ccc2c(c1)OCO2
Agent: [Na+]
Agent: [OH-]
Solvent: C1COCCO1
Solvent: O
Product: CC(C)N(C(N)=S)c1ccc2c(c1)OCO2
Temperature: 15 °C

Procedure:
To a stirred solution consisting of 45 ml. of dioxane and 200 ml. of water is added 27 grams of sodium hydroxide and the whole stirred until complete solution takes place. To this solution is added 17 grams of N-isopropyl-N-(3,4-methylenedioxyphenyl)-N'-benzoyl thiourea. The resulting mixture is heated to reflux for 48 hours and then cooled to 15°C. The resulting white solid is crystallized from benzene to obtain N-isopropyl-N-(3,4-methylenedioxyphenyl)-thiourea melting at 149°-151°C.