(2-Benzylamino-3-nitro-6-trifluoromethyl-pyridin-4-yl)-carbamic acid ethyl ester → (3-Amino-2-benzylamino-6-trifluormethyl-pyridin-4-yl)-carbamic acid ethyl ester

HRID 639631Notes

Reaction equation

HRID 639631 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[NH:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]=1[N+:24]([O-])=O)[CH3:2].[H][H]>C(O)C.[Ni]>[CH2:1]([O:3][C:4](=[O:27])[NH:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]=1[NH2:24])[CH3:2]

Participants

5

Reactant 2

HCID 67456211(2-Benzylamino-3-nitro-6-trifluoromethyl-pyridin-4-yl)-carbamic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 67455304(3-Amino-2-benzylamino-6-trifluormethyl-pyridin-4-yl)-carbamic acid ethyl esterYield 99.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

(2-benzylamino-3-nitro-6-trifluormethyl-pyridin-4-yl)-carbamic acid ethyl ester (95 mg, 0.25 mmol) was dissolved in 10 mL of ethanol and Raney Nickel (20 mg, 20% MW) was added then the reaction mixture was stirred at room temperature in a bomb under 50 PSI of hydrogen for 2 h. The mixture was filtered through arbocel and the filtrate was concentrated in vacuo to give 88 mg of the title compound as a pale green gum.

Workup

  1. filtrationThe mixture was filtered through arbocel
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b8ecb760d2624a199279fc1a2051ad43
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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