4-Methoxybenzylamine → Methyl 2-fluoro-4-(4-methoxybenzylamino)-5-nitrobenzoate

HRID 1403600Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10](F)[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CCN(C(C)C)C(C)C.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1>CN(C)C=O.O>[F:1][C:2]1[CH:11]=[C:10]([NH:32][CH2:31][C:30]2[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of methyl 2,4-difluoro-5-nitrobenzoate (35 g, 161.20 mmol) in N,N-dimethylformamide (1000 ml) was added DIEA (41.3 g, 319.56 mmol). Then (4-methoxybenzylamine (28.72 g, 209.64 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-fluoro-4-(4-methoxybenzylamino)-5-nitrobenzoate as a yellow solid (44 g, 82%).

Workup

filtrationThe solids were collected by filtration

Sources & evidence

ORD record: ord-e3e2be3bc682415b8086e8d681525a95
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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