4-Fluoro-3-nitroaniline → HCID 86629434, compound

HRID 599263Notes

Reaction equation

HRID 599263 reaction equation
Cl.Cl[CH2:3][C:4]1[C:5]([NH:14][CH3:15])=[CH:6][C:7]([N:10]([O:12][CH3:13])[CH3:11])=[N:8][CH:9]=1.[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]>N1C=CC=CC=1>[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][CH2:3][C:4]2[C:5]([NH:14][CH3:15])=[CH:6][C:7]([N:10]([O:12][CH3:13])[CH3:11])=[N:8][CH:9]=2)=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]

Participants

4

Reactant 2

HCID 677684-Fluoro-3-nitroanilineHCID 86629435HCID 86629435, compound

Product 1

HCID 86629434HCID 86629434, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of the above 5-(chloromethyl)-N2-methoxy-N2,N4-dimethylpyridine-2,4-diamine HCl (3.5 g, 16.3 mmol) and 4-fluoro-3-nitroaniline (41.5 mL, 0.3 mol) in pyridine (150 mL) was stirred at 50° C. for 8 h. The reaction mixture was concentrated in vacuo to afford a crude product which was washed with H2O and dried to give 5-((4-fluoro-3-nitrophenylamino)methyl)-N2-methoxy-N2,N4-dimethylpyridine-2,4-diamine (3.3 g, 60% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.83 (m, 1 H), 7.62 (s, 1 H), 7.30 (t, J=9.2 Hz, 1 H), 7.20 (m, 1 H), 6.98 (m, 1 H), 6.81 (s, 1 H), 5.98 (s, 1 H), 4.14 (s, 2 H), 3.69 (s, 3 H), 3.30 (s, 3H), 2.89 (d, J=4.8 Hz, 3 H); MS (ESI) m/z: 336.2 (M+H+)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto afford a crude product which
  3. washwas washed with H2O
  4. customdried

Sources & evidence

ORD record
ord-2dba02bf276941f48401b9e8f369c0d7
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

Loading…