4-Methoxybenzylamine → HCID 70665192, compound

HRID 1403585Notes

Reaction equation

F[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:15][CH3:16])[CH:3]=1.CCN(C(C)C)C(C)C.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][NH2:35])=[CH:30][CH:29]=1>CN(C)C=O.O>[CH3:16][O:15][C:4]1[CH:3]=[C:2]([NH:35][CH2:34][C:31]2[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=2)[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of methyl 4-fluoro-2-methoxy-5-nitrobenzoate (40 g, 174.55 mmol) in N,N-dimethylformamide (1000 mL) was added DIEA (45.2 g, 349.74 mmol). Then (4-methoxyphenyl)methanamine (31.1 g, 226.71 mmol) was added dropwise with stirring for 1 hour at 25° C. The reaction mixture was diluted with water (2 L). The solids were collected by filtration to afford methyl 2-methoxy-4-(4-methoxybenzylamino)-5-nitrobenzoate as a yellow solid (44 g, 75%).

Workup

filtrationThe solids were collected by filtration

Sources & evidence

ORD record: ord-251627efac5c4b03b25b158e7af23061
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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