Dichloromethane methanol → HCID 90415876, compound

HRID 1428600Notes

Reaction equation

HRID 1428600 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][O:5][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.C(Cl)Cl.CO>CO.[Pd]>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][O:5][C:6]1[N:7]=[CH:8][C:9]([NH2:16])=[CH:10][C:11]=1[C:12]([F:15])([F:13])[F:14]

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 90415383HCID 90415383, compound

Product 1

HCID 90415876HCID 90415876, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N,N-dimethyl-2-((5-nitro-3-(trifluoromethyl)pyridin-2-yl)oxy)ethanamine (500 mg, 1.791 mmol) and Pd/C (191 mg, 1.791 mmol) in MeOH (30 mL) was stirred at 20° C. under H2. After TLC analysis (DCM/MeOH=20/1) showed the starting material had disappeared, the mixture was filtered. The filtrate was concentrated to yield a oil of 6-(2-(dimethylamino)ethoxy)-5-(trifluoromethyl)pyridin-3-amine (360 mg, 1.444 mmol, 81.1% yield): 1H NMR (400 MHz, CD3OD) δ 7.77 (d, J=2.4 Hz, 1H), 7.37 (d, J=3.2 Hz, 1H), 4.43 (t, J=5.6 Hz, 2H), 2.78 (t, J=6.4 Hz, 2H), 2.35 (s, 6H); ES-LCMS m/z 250.1 (M+H).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-31ceca2a42cd42b0bd91b4aa174f6772
Source dataset
uspto-grants-2015_01
Patent number
US08937071B2

Reaction notes

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