1-Isopropylhydrazine hydrochloride → HCID 59734395, compound

HRID 1098573Notes

Reaction equation

HRID 1098573 reaction equation
Cl.[CH:2]([NH:5][NH2:6])([CH3:4])[CH3:3].[C:7]([C:10](=[C:16]=CN(C)C)[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=O)[CH3:8]>>[CH:2]([N:5]1[C:7]([CH3:8])=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:16]=[N:6]1)([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 855731-Isopropylhydrazine hydrochlorideHCID 86623854HCID 86623854, compound

Product 1

HCID 59734395HCID 59734395, compound

Procedure

In a procedure analogous to Example B6, isopropylhydrazine hydrochloride (896 mg, 8.10 mmol) and ethyl 2-acetyl-3-(dimethylaminomethylene)acrylate (1.50 g, 8.10 mmol) were combined and purified by chromatography (ethyl acetate/hexane) to afford ethyl 1-isopropyl-5-methyl-1H-pyrazole-4-carboxylate (faster elution, 537 mg), 1H NMR (300 MHz, DMSO-d6): δ 1.30 (t, 3 H), 1.39 (d, 6 H), 4.23 (q, 2 H), 4.61 (hp, 1 H), 7.82 (s, 1 H); MS (ESI) m/z: 197.0 (M+H+) and ethyl 1-isopropyl-3-methyl-1H-pyrazole-4-carboxylate (slower elution, 91 mg), 1H NMR (300 MHz, DMSO-d6), δ 1.29 (t, 3 H), 1.42 (d, 6 H), 2.36 (s, 3 H), 4.21 (q, 2 H), 4.49 (hp, 1 H), 8.24 (s, 1 H); MS (ESI) m/z: 197.0 (M+H+).

Workup

  1. custompurified by chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-77322bffeef4474ab10029cb6cf9903d
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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