4-Methoxybenzylamine → Methyl 4-[[(4-methoxyphenyl)methyl]amino]-3-nitrobenzoate

HRID 1520132Notes

Reaction equation

HRID 1520132 reaction equation
CCN(C(C)C)C(C)C.F[C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][NH2:33])=[CH:28][CH:27]=1>CN(C)C=O.O>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][NH:33][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=2[N+:21]([O-:23])=[O:22])=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 754524-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 53396459Methyl 4-[[(4-methoxyphenyl)methyl]amino]-3-nitrobenzoateYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIEA (389.0 g, 3.02 mol) was added to a solution of methyl 4-fluoro-3-nitrobenzoate (200.0 g, 1.00 mol) in N,N-dimethylformamide (2 L) at room temperature. Then (4-methoxyphenyl)methanamine (275 g, 2.00 mol) was added dropwise. After 2 h, the reaction was diluted with water (5 L), the solids were collected by filtration to afford methyl 4-(4-methoxybenzylamino)-3-nitrobenzoate as a yellow solid (250 g, 78%).

Workup

  1. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-17e610466ca043d48c1d821b4a6b1222
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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