Diethyl (ethoxymethylene)malonate → ethyl 5-hydroxy-1-(2-methylphenyl)-1H-pyrazole-4-carboxylate

HRID 2095810Notes

Reaction equation

HRID 2095810 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][NH2:9].Cl.C(=O)([O-])[O-].[K+].[K+].C([O:19][CH:20]=[C:21]([C:27](OCC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])C>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20](=[O:19])[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][NH:9]1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11430Potassium CarbonateHCID 71554o-Tolylhydrazinium(1+) chloride

Product 1

HCID 10037547ethyl 5-hydroxy-1-(2-methylphenyl)-1H-pyrazole-4-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In the same manner as in Reference Example 63 and using (2-methylphenyl)hydrazine•hydrochloride (5 g, 32 mmol), water (100 mL), potassium carbonate (9.7 g, 70 mmol) and diethyl ethoxymethylenemalonate (8.3 g, 38 mmol) as starting materials, the title compound (6.8 g, 87%) was obtained as a brown solid.

Sources & evidence

ORD record
ord-fc04d8391d124aa6a198cb848ae4c526
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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