Aniline → 3'-Amino-6-chloro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

HRID 77715Notes

Reaction equation

HRID 77715 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)=[CH:6][C:5]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[O:18])=[CH:4][CH:3]=1.NC1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:14][C:10]1[CH:9]=[C:8]([C:7]2[C:2]([Cl:1])=[CH:3][CH:4]=[C:5]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=3)=[O:18])[CH:6]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 692724446-Chloro-3'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

Product 1

HCID 692744463'-Amino-6-chloro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamideYield 76.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

6-Chloro-3′-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide (0.46 g, 0.0011 mol) was dissolved in methanol (40 mL), and palladium hydroxide on carbon (20%; 88 mg; 50% wet; 0.000063 mol) was added. The resulting mixture was hydrogenated at 60 psi and 20° C. for 20 h, at which time LCMS showed near complete conversion to the aniline (accompanied by 3% de-chlorination). The reaction mixture was filtered; and rinsed thoroughly. The filtrate was concentrated in vacuo to give 0.33 g of product. The product was purified by prep HPLC/MS using a 30 mm×100 mm C18 column; 35% CH3CN—H2O (0.1% TFA), 1 min, to 55% at 6 min; 60 mL/min; detector set at m/z 391; retention time, 5.5 min. The resulting mixture was freeze dried to yield 258 mg white solid TFA salt. 1H NMR (DMSO-d6) δ 10.62 (br s, 1H, amide NH); 8.20 (s, 1H); 8.04 (d, 1H); 8.00 (m, 2H); 7.75 (d, 1H); 7.59 (t, 1H); 7.45 (d, 1H); 7.35 (t, 1H); 7.00 (m, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washand rinsed thoroughly
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d6a5a5d3fd714b41b98e2d5e8f2d1906
Source dataset
uspto-grants-2014_09
Patent number
US08841318B2

Reaction notes

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