3-Chloro-4-fluoroaniline → 4-(3-Chloro-4-fluoro-phenylamino)-6-nitro-[1.8]naphthyridine-3-carbonitrile

HRID 276833Notes

Reaction equation

HRID 276833 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[F:25])[NH2:21]>>[Cl:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[C:6](=[N:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][C:24]=1[F:25]

Participants

3

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 155506564-Chloro-6-nitro-1,8-naphthyridine-3-carbonitrile

Product 1

HCID 98845174-(3-Chloro-4-fluoro-phenylamino)-6-nitro-[1.8]naphthyridine-3-carbonitrileYield 95.8%

Procedure

By using the method of Example 21, 2.5 g (10.66 mmol) of 4-chloro-6-nitro-[1.8]naphthyridine-3-carbonitrile and 1.55 g (10.66 mmol) of 3-chloro-4-fluoro-aniline was converted to 3.51 g of the title compound, a yellow solid, as its hydrochloride salt: mass spectrum (electrospray, m/e): M+H 344.1.

Sources & evidence

ORD record
ord-444454b929d447e5b89524eeab77d143
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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