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

HRID 77705Notes

Reaction equation

HRID 77705 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-e6d9f373ce19468fad957ffed80da12a
Source dataset
uspto-grants-2014_09
Patent number
US08841318B2

Reaction notes

Loading…