Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: CO.[O:3]1CCO[CH:4]1[C:8]1[CH:21]=[CH:20][C:11]([CH2:12][NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[C:14]1([NH:13][CH2:12][C:11]2[CH:10]=[CH:9][C:8]([CH:4]=[O:3])=[CH:21][CH:20]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
Reactant: c1ccc(NCc2ccc(C3OCCO3)cc2)cc1
Agent: Cl
Agent: O=C([O-])O
Agent: [Na+]
Solvent: C1CCOC1
Solvent: CO
Product: O=Cc1ccc(CNc2ccccc2)cc1
Temperature: 25 °C
Reaction time: 1 h
Yield: 101.6 %

Procedure:
To a mixture solution of methanol and tetrahydrofuran (1:1, 20 mL) of (4-[1,3]dioxolane-2-yl-benzyl)-phenyl-amine (4.16 g, 16.3 mmol) described in Manufacturing Example 73-1-2 was added 5N hydrochloric acid (20 mL). This mixture was stirred for 1 hour at room temperature. This mixture was neutralized with saturated aqueous sodium hydrogencarbonate solution, and extracted with ethyl acetate. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (3.5 g). This compound was used in the subsequent reaction without being purified.