Diethyl (ethoxymethylene)malonate → HCID 178469976, compound

HRID 386377

Reaction equation

HRID 386377 reaction equation
Cl.[C:2]1([NH:12][NH2:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C([O:22][CH:23]=[C:24]([C:30](OCC)=O)[C:25]([O:27][CH2:28][CH3:29])=[O:26])C>O>[OH:22][C:23]1[N:12]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][CH:3]=2)[N:13]=[CH:30][C:24]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11430Potassium CarbonateHCID 519949Hydrazine, 1-naphthalenyl-, hydrochloride (1:1)

Product 1

HCID 178469976HCID 178469976, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of naphthalen-1-ylhydrazine hydrochloride (1 g, 5.1 mmol) and potassium carbonate (1.4 g, 10.3 mmol) in water (30 mL) was added diethyl ethoxymethylenemalonate (1.1 g, 5.1 mmol) at room temperature. The reaction mixture was stirred for 3 hours at room temperature and then extracted with ethyl acetate. The aqueous layer was acidified with 1N HCl to pH 2 and then extracted with ethyl acetate again. This organic layer was dried over sodium sulfate and concentrated to give ethyl 5-hydroxy-1-(naphthalen-1-yl)-1H-pyrazole-4-carboxylate as a solid.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted with ethyl acetate again
  3. dry with materialThis organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cbc4fcad5bc1492d851e5efcf9e3c2eb
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Linked notes

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