Methylhydrazine → Ethyl 5-(4-chlorobutyl)-1-methyl-1H-pyrazole-3-carboxylate

HRID 2283827Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=O)[CH3:7].[C:9](OCC)(=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH3:19][NH:20][NH2:21]>>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:20]([CH3:19])[N:21]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=1

Participants

Reactant 3

HCID 6061Methylhydrazine

HCID 7268Diethyl Oxalate

HCID 824686-Chlorohexan-2-one

Product 1

HCID 66959070Ethyl 5-(4-chlorobutyl)-1-methyl-1H-pyrazole-3-carboxylate

Procedure

Ethyl 5-(4-chlorobutyl)-1-methyl-1H-pyrazole-3-carboxylate was prepared from 6-chloro-2-hexanone (50.0 g, 357 mmol) and diethyl oxalate (48.4 mL, 357 mmol) according to the procedure described in Part A of Example 19 using methyl hydrazine (19.0 mL, 357 mmol) in place of ethylhydrazine oxalate. Ethyl 5-(4-chlorobutyl)-1-methyl-1H-pyrazole-3-carboxylate was isolated as a dark oil that was used without purification in the next step.

Sources & evidence

ORD record: ord-0f655df7f57f481ebda68f5df3719cf6
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145410B2

Reaction notes

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