1-Isopropylhydrazine hydrochloride → Ethyl 1-(1-methylethyl)-1H-pyrazole-5-carboxylate

HRID 873853Notes

Reaction equation

HRID 873853 reaction equation
Cl.[CH:2]([NH:5][NH2:6])([CH3:4])[CH3:3].CN(C)[CH:9]=[CH:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>>[CH:2]([N:5]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=[N:6]1)([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 855731-Isopropylhydrazine hydrochlorideHCID 2777802Ethyl 4-(dimethylamino)-2-oxo-but-3-enoate

Product 1

HCID 23005968Ethyl 1-(1-methylethyl)-1H-pyrazole-5-carboxylate

Procedure

The title compound was prepared in analogy to the procedure described in Step 17.3 using isopropylhydrazine hydrochloride and ethyl 4-(dimethylamino)-2-oxobut-3-enoate at 120° C. for hr. The crude product was purified by silica gel column chromatography (hexane/EtOAc 2.5-40%). tR: 4.74 min (HPLC 1); tR: 1.00 min (LC-MS 2); ESI-MS: 183 [M+H]+ (LC-MS 2); Rf=0.95 (hexane/EtOAc 1:1).

Workup

  1. customThe crude product was purified by silica gel column chromatography (hexane/EtOAc 2.5-40%)

Sources & evidence

ORD record
ord-86d3d410267b472ebd8fb4e4ec51704d
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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