Ammonium Hydroxide → N-(4'-Amino-6-methylbiphenyl-3-yl)-3-(trifluoromethyl)benzamide

HRID 1894877Notes

Reaction equation

HRID 1894877 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]([NH:17][C:18](=[O:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)=[CH:4][CH:3]=1.O1CCOCC1.[OH-].[NH4+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]([NH:17][C:18](=[O:29])[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=3)[CH:6]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 312751,4-DioxaneHCID 69273794N-(6-Methyl-4'-nitrobiphenyl-3-yl)-3-(trifluoromethyl)benzamide

Product 1

HCID 69046998N-(4'-Amino-6-methylbiphenyl-3-yl)-3-(trifluoromethyl)benzamideYield 44.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To N-(6-methyl-4′-nitrobiphenyl-3-yl)-3-(trifluoromethyl)benzamide (375 mg, 0.937 mmol) was added 1,4-dioxane (12 mL) and water (6.2 mL), then ammonium hydroxide (220 μL, 5.6 mmol) followed by sodium dithionite (1.4 g, 7.9 mmol). The reaction was stirred at ambient temperature until LCMS indicated complete reduction, typically 30-60 minutes. The reaction is accompanied by a color change from yellow to colorless. The reaction was partitioned between water and EtOAc and the organic phase was washed with water and saturated aqueous NaCl, then dried (MgSO4) and evaporated to leave the crude product (155 mg, 44.8%) which was used without further purification in the subsequent reaction. MS (EI) m/z=371 (M+H).

Workup

  1. customreduction, typically 30-60 minutes
  2. customThe reaction was partitioned between water and EtOAc
  3. washthe organic phase was washed with water and saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-67786159925e4ff1bfdf53f62f5b753a
Source dataset
uspto-grants-2013_08
Patent number
US08513270B2

Reaction notes

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