Ethyl Acetate → 2-(5-Amino-3-(trifluoromethyl)pyridin-2-yl)-2-methylpropan-1-ol

HRID 1050129Notes

Reaction equation

HRID 1050129 reaction equation
[CH3:1][C:2]([C:6]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]([N+:16]([O-])=O)=[CH:8][N:7]=1)([CH3:5])[CH:3]=[O:4].CC(=O)OCC>[Ni].CO>[NH2:16][C:9]1[CH:10]=[C:11]([C:12]([F:15])([F:13])[F:14])[C:6]([C:2]([CH3:5])([CH3:1])[CH2:3][OH:4])=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 904224602-Methyl-2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)propanal

Product 1

HCID 904232762-(5-Amino-3-(trifluoromethyl)pyridin-2-yl)-2-methylpropan-1-olYield 67.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-methyl-2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)propanal (100 mg, 0.381 mmol) and Raney nickel (22.39 mg, 0.381 mmol) in MeOH (30 mL) was stirred at 25° C. under H2 overnight. After TLC analysis (PE/EA=5/1) showed the starting material was consumed, the mixture was filtered. The filtrate was concentrated to give 2-(5-amino-3-(trifluoro methyl)pyridin-2-yl)-2-methylpropan-1-ol (60 mg, 0.256 mmol, 67% yield): 1H NMR (400 MHz, CD3OD) δ 8.08 (br. s., 1H), 7.36 (d, J=2.8 Hz, 1H), 1.31 (s, 6H); ES-LCMS m/z: 235.1 (M+H).

Workup

  1. customwas consumed
  2. filtrationthe mixture was filtered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-485c5b417fed4492978398f54fececae
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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