3-Chloro-4-fluoroaniline → N-(4-Fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-amino-benzoic acid amide

HRID 410111Notes

Reaction equation

HRID 410111 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:22])[C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[C:13]([NH:19][CH3:20])=[CH:12][C:11]=2[F:21])=[CH:4][C:3]=1[Cl:23].FC1C=C(NC)C([N+]([O-])=O)=CC=1C(O)=O.FC1C=CC(N)=CC=1Cl>[Ni]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:22])[C:10]2[CH:15]=[C:14]([NH2:16])[C:13]([NH:19][CH3:20])=[CH:12][C:11]=2[F:21])=[CH:4][C:3]=1[Cl:23]

Participants

5

Reactant 3

HCID 97083-Chloro-4-fluoroanilineHCID 595298342-Fluoro-4-(methylamino)-5-nitrobenzoic acidHCID 67957648N-(4-Fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-nitro-benzoic acid amide

Product 1

HCID 68052224N-(4-Fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-amino-benzoic acid amide

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

The subtitle compound is prepared from N-(4-fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-nitro-benzoic acid amide (prepared from 2-fluoro-4-methylamino-5-nitro-benzoic acid, 4-fluoro-3-chloro-aniline in analogy to the step 6a) with RaNi and H2 in analogy to example 5c.

Sources & evidence

ORD record
ord-ceffd051565744838254188dc4a6cfaf
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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