Pentanenitrile, 4,4-dimethyl-3-oxo- → ethyl 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1-naphthoate

HRID 1696485Notes

Reaction equation

HRID 1696485 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]([NH:17][NH2:18])[CH:8]=1)=[O:6])[CH3:3].[CH3:19][C:20]([CH3:27])([CH3:26])[C:21](=O)[CH2:22][C:23]#[N:24]>CCO.Cl>[NH2:24][C:23]1[N:17]([C:9]2[CH:8]=[C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[C:16]3[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:18]=[C:21]([C:20]([CH3:27])([CH3:26])[CH3:19])[CH:22]=1

Participants

5

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 67271149Ethyl 3-hydrazinonaphthalene-1-carboxylate hydrochloride

Product 1

HCID 58851682ethyl 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1-naphthoateYield 95.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 3-hydrazinonaphthalene-1-carboxylic acid ethyl ester hydrochloride (1.5 g, 5.6 mmol) and 4,4-dimethyl-3-oxopentanenitrile (875 mg, 7.0 mmol) in EtOH (50 mL) and conc. HCl (5 mL) was heated at reflux overnight. After removal of the solvent, the residue was purified by column chromatography to yield ethyl 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1-naphthoate (1.8 g, 95% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.74 (d, J=6.3 Hz, 1H), 8.47 (s, 1H), 8.24 (s, 1H), 8.15 (d, J=6.0 Hz, 1H), 7.76 (t, J=5.7 Hz, 1H), 7.71 (t, J=5.7 Hz, 1H), 5.68 (s, 1H), 4.44 (q, J=5.4 Hz, 2H), 1.37 (t, J=5.4 Hz, 3H), 1.30 (s, 9H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customAfter removal of the solvent
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-cb1abdcf015d40cf81e2b326efb74600
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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