2-Chlorophenylhydrazine hydrochloride → methyl 1-(2-chlorophenyl)-5-(furan-2-yl)-1H-pyrazole-3-carboxylate

HRID 877436Notes

Reaction equation

HRID 877436 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[CH2:7][C:8](=O)[C:9]([O:11][CH3:12])=[O:10].Cl.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][NH2:24]>CO>[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[N:24]1

Participants

4

Reactant 2

HCID 4432872-Chlorophenylhydrazine hydrochlorideHCID 2771615Methyl 4-(furan-2-yl)-2,4-dioxobutanoate

Product 1

HCID 43513895methyl 1-(2-chlorophenyl)-5-(furan-2-yl)-1H-pyrazole-3-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution compound 5 (10.0 g, 50 mmol) and (2-chlorophenyl)hydrazine hydrochloride (10.0 g, 56 mmol) in methanol 80 mL was heated to reflux for 6 h. On cooling to 0° C., solid crashed out, filtered and washed with cold methanol to afford the title compound 6 (12.0 g, 80.0%) which was used for further reaction.

Workup

  1. temperatureto reflux for 6 h
  2. filtrationfiltered
  3. washwashed with cold methanol

Sources & evidence

ORD record
ord-703c3e6eccc94c9688814495f9212eee
Source dataset
uspto-grants-2015_03
Patent number
US08987318B2

Reaction notes

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