Acetic acid, 2-(3-hydrazinophenyl)-, ethyl ester → HCID 67272221, compound

HRID 1696451Notes

Reaction equation

HRID 1696451 reaction equation
[NH:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1)[NH2:2].[F:15][C:16]([F:23])([F:22])[C:17](=O)[CH2:18][C:19]#[N:20]>CCO>[NH2:20][C:19]1[N:1]([C:3]2[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=2)[N:2]=[C:17]([C:16]([F:23])([F:22])[F:15])[CH:18]=1

Participants

4

Reactant 2

HCID 578094Acetic acid, 2-(3-hydrazinophenyl)-, ethyl esterHCID 138435404,4,4-Trifluoro-3-oxobutanenitrile

Product 1

HCID 67272221HCID 67272221, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (3-hydrazinophenyl)acetate (8.77 g, 0.028 mol, available from Example A5) and 4,4,4-trifluoro-3-oxo-butyronitrile (5.75 g, 0.042 mol) in EtOH (200 mL) was heated at reflux overnight. The mixture was concentrated and the residue purified by column chromatography to yield ethyl 2-(3-(5-amino-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)acetate (5 g, 57% yield) as a yellow oil. 1H NMR (300 MHz, DMSO-d6): 7.50-7.43 (m, 3H), 7.30-7.33 (m, 1H), 5.81 (s, 1H), 5.75 (s, 2H), 4.09 (q, J=7.2 Hz, 1H), 3.76 (s, 2H), 3.38 (s, 2H), 1.18 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 314 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated
  4. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-36cfd237618e43c1b223254f71efbcc9
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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