Hydrochloric Acid → Ethyl 2-amino-4-bromo-6-(trifluoromethyl)phenyl[3-(trifluoromethyl)benzyl]carbamate

HRID 495654Notes

Reaction equation

HRID 495654 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([N:12]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:4]([N+:29]([O-])=O)[CH:3]=1.[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:29][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[C:5]=1[N:12]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[CH:20]=1)[C:13](=[O:17])[O:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 22327411Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl[3-(trifluoromethyl)benzyl]carbamate

Product 1

HCID 22327386Ethyl 2-amino-4-bromo-6-(trifluoromethyl)phenyl[3-(trifluoromethyl)benzyl]carbamateYield 100.4%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl[3-(trifluoromethyl)benzyl]carbamate (225.7 mg) and nickel(II) chloride hexahydrate (211.9 mg) in methanol (5 ml) was added sodium borohydride (71.7 mg) in an ice bath. After the mixture was stirred for 10 minutes, 1N hydrochloric acid was added. The mixture was basified with saturated aqueous sodium bicarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (213.4 mg, quantitative yield).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-caa9a37731cd40e29bc404388b356a7d
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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