3-Bromo-4-fluoroaniline → 4-(3-bromo-4-fluorophenylamino)-1-methyl-3-nitro-1H-pyridin-2-one

HRID 2180033Notes

Reaction equation

HRID 2180033 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]([CH3:8])[C:4](=[O:9])[C:3]=1[N+:10]([O-:12])=[O:11].[Br:13][C:14]1[CH:15]=[C:16]([NH2:21])[CH:17]=[CH:18][C:19]=1[F:20]>>[Br:13][C:14]1[CH:15]=[C:16]([NH:21][C:2]2[CH:7]=[CH:6][N:5]([CH3:8])[C:4](=[O:9])[C:3]=2[N+:10]([O-:12])=[O:11])[CH:17]=[CH:18][C:19]=1[F:20]

Participants

3

Reactant 2

HCID 27792863-Bromo-4-fluoroanilineHCID 224903014-Chloro-1-methyl-3-nitro-1,2-dihydropyridin-2-one

Product 1

HCID 224902994-(3-bromo-4-fluorophenylamino)-1-methyl-3-nitro-1H-pyridin-2-oneYield 40%

Procedure

4-Chloro-1-methyl-3-nitro-1H-pyridin-2-one was coupled to 3-bromo-4-fluorophenylamine, in the same way as in Example 1, to give 4-(3-bromo-4-fluorophenylamino)-1-methyl-3-nitro-1H-pyridin-2-one as a beige solid (2.0 g, 40%): δH (400 MHz, d6-DMSO) 3.36 (3H, s), 5.81 (1H, d, J 8), 7.33-7.37 (1H, m), 7.45 (1H, t, J 9), 7.64-7.68 (1H, m), 7.66 (1H, s), 9.73 (1H, s).

Sources & evidence

ORD record
ord-ff51c422c8ab470fa68f4e6b998d53aa
Source dataset
uspto-grants-2005_05
Patent number
US06887885B2

Reaction notes

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