4-Fluoro-3-nitroaniline → HCID 86629447, compound

HRID 599290Notes

Reaction equation

HRID 599290 reaction equation
Cl[CH2:2][C:3]1[C:4]([NH:13][CH2:14][CH3:15])=[CH:5][C:6]([N:9]([O:11][CH3:12])[CH3:10])=[N:7][CH:8]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]>N1C=CC=CC=1>[CH2:14]([NH:13][C:4]1[C:3]([CH2:2][NH:23][C:20]2[CH:21]=[CH:22][C:17]([F:16])=[C:18]([N+:24]([O-:26])=[O:25])[CH:19]=2)=[CH:8][N:7]=[C:6]([N:9]([O:11][CH3:12])[CH3:10])[CH:5]=1)[CH3:15]

Participants

4

Reactant 2

HCID 677684-Fluoro-3-nitroanilineHCID 86629448HCID 86629448, compound

Product 1

HCID 86629447HCID 86629447, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-(Chloromethyl)-N4-ethyl-N2-methoxy-N2-methylpyridine-2,4-diamine (4.3 g, 18.7 mmol, from Example A19) and 4-fluoro-3-nitro-phenylamine (3 g, 19 mmol) were combined in pyridine (50 ml) by the method of Example A4 to provide N4-ethyl-5-((4-fluoro-3-nitrophenylamino)methyl)-N2-methoxy-N2-methylpyridine-2,4-diamine (5.6 g, 85% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.65 (s, 1 H), 7.63 (s, 1 H), 7.34-7.29 (m, 1 H), 7.23-7.21 (m, 1H), 7.02-7.6.98 (m, 1 H), 6.84 (s, 1 H), 6.06 (s, 1 H), 4.18 (d, J=3.2 Hz, 2 H), 3.71 (s, 3 H), 3.31 (s, 3 H), 3.32 (q, J=7.2 Hz, 2 H), 1.18 (t, J=7.2 Hz, 3 H); MS (ESI) m/z: 350.1 [M+H]+.

Sources & evidence

ORD record
ord-6a3d20a8e83148a0a669f508974cb93e
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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