Ethanol → ethyl 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate

HRID 1392317Notes

Reaction equation

HRID 1392317 reaction equation
Cl.[NH:2]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])[NH2:3].[CH3:13][C:14]([CH3:21])([CH3:20])[C:15](=O)[CH2:16][C:17]#[N:18].[CH2:22](O)[CH3:23]>>[CH2:22]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N:2]2[C:17]([NH2:18])=[CH:16][C:15]([C:14]([CH3:21])([CH3:20])[CH3:13])=[N:3]2)[CH:5]=1)[CH3:23].[NH2:18][C:17]1[N:2]([C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=2)[C:7]([OH:9])=[O:8])[N:3]=[C:15]([C:14]([CH3:21])([CH3:20])[CH3:13])[CH:16]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 128918633-Hydrazinobenzoic acid hydrochloride

Product 2

HCID 218672843-(3-tert-butyl-5-amino-1H-pyrazol-1-yl)benzoic acidYield 36%HCID 21867322ethyl 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoateYield 40%

Procedure

A mixture of 3-hydrazino-benzoic acid hydrochloride (200 g, 1.06 mol) and 4,4-dimethyl-3-oxo-pentanenitrile (146 g, 1.167 mol) in ethanol (2 L) was heated to reflux overnight. The reaction solution was evaporated under reduced pressure. The residue was purified by column chromatography to give 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid ethyl ester (116 g, 40%) as a white solid together with 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid (93 g, 36%). 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid and ethyl ester: 1H NMR (DMSO-d6): 8.09 (s, 1 H), 8.05 (brd, J=8.0 Hz, 1 H), 7.87 (br d, J=8.0 Hz, 1 H), 7.71 (t, J=8.0 Hz, 1 H), 5.64 (s, 1 H), 4.35 (q, J=7.2 Hz, 2 H), 1.34 (t, J=7.2 Hz, 3 H), 1.28 (s, 9H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe reaction solution was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-34fa235c70484754a807d4283b3bd9d9
Source dataset
uspto-grants-2008_03
Patent number
US07342037B2

Reaction notes

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