Water → 4'-Amino-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

HRID 1894883Notes

Reaction equation

HRID 1894883 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][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.O1CCOCC1.O.[OH-].[NH4+].S(S([O-])=O)([O-])=O.[Na+].[Na+].NC1C=CC=CC=1>>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=3)=[O:18])[CH:6]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 6

HCID 962WaterHCID 6115AnilineHCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 312751,4-DioxaneHCID 690428606-Methyl-4'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

Product 1

HCID 690431094'-Amino-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

Conditions

Temperature
25 °C

Procedure

6-Methyl-4′-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide was dissolved in 1,4-dioxane (10.00 mL, 0.1281 mol) and water (5.00 mL, 0.278 mol), and ammonium hydroxide (0.18 mL, 0.0045 mol) was added. To the reaction was added sodium dithionite (1.10 g, 0.00632 mol) and this mixture was stirred at 25° C. for 2 hours at which time HPLC analysis showed aniline formation. The reaction was extracted with ethyl acetate and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and concentrated in vacuo. MS (EI) m/z=371 (M+H).

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. washthe organic extracts were washed with water, saturated NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fcedce4e3c04c45a9efd8a4a77f8d19
Source dataset
uspto-grants-2013_08
Patent number
US08513270B2

Reaction notes

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