2-Chloro-4-fluoro-5-nitroaniline → HCID 86629440, compound

HRID 599282Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[NH2:12].Cl[CH2:14][C:15]1[C:16]([NH:25][CH3:26])=[CH:17][C:18]([N:21]([O:23][CH3:24])[CH3:22])=[N:19][CH:20]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[NH:12][CH2:14][C:15]1[C:16]([NH:25][CH3:26])=[CH:17][C:18]([N:21]([O:23][CH3:24])[CH3:22])=[N:19][CH:20]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Chloro-4-fluoro-5-nitro-phenylamine (1.4 g, 7.4 mmol) was added to a solution of 5-(chloromethyl)-N2-methoxy-N2,N4-dimethylpyridine-2,4-diamine from example A16 (1.6 g, 7.4 mmol) in pyridine (30 mL) and the mixture was stirred at 50° C. for 8 hours. The reaction mixture was concentrated under reduced pressure and the solid residue was thoroughly washed with water to give 5-((2-chloro-4-fluoro-5-nitrophenylamino)methyl)-N2-methoxy-N2,N4-dimethylpyridine-2,4-diamine (1.5 g, 56% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.01 (s, 1H), 7.76 (d, J=8.4 Hz, 1 H), 7.71 (s, 1 H), 7.34 (d, J=8 Hz, 1 H), 6.56 (m, 1 H), 5.98 (s, 1 H), 4.36 (d, J=4 Hz, 2 H), 3.71 (s, 3 H), 3.31 (s, 3 H), 2.91-2.92 (d, J=4 Hz, 3 H); MS (ESI) m/z: 369.9 [M+H]+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
washthe solid residue was thoroughly washed with water

Sources & evidence

ORD record: ord-dc2dde2bdcd2470493bad7a8e9291bd4
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897762B2

Reaction notes

Loading…