Ethyl Acetoacetate → HCID 19923023, compound

HRID 2254132Notes

Reaction equation

HRID 2254132 reaction equation
Cl.[CH:2]1([NH2:5])[CH2:4][CH2:3]1.[C:6]([O:12][CH2:13][CH3:14])(=[O:11])[CH2:7][C:8]([CH3:10])=O.[F:15][C:16]([F:33])([F:32])[C:17]1[CH:31]=[CH:30][C:20]([CH:21]=[C:22]([C:27]([CH3:29])=O)[C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH:2]1([N:5]2[C:8]([CH3:10])=[C:7]([C:6]([O:12][CH2:13][CH3:14])=[O:11])[CH:21]([C:20]3[CH:30]=[CH:31][C:17]([C:16]([F:33])([F:32])[F:15])=[CH:18][CH:19]=3)[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:27]2[CH3:29])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 11708049Cyclopropylamine hydrochlorideHCID 54435405HCID 54435405, compound

Product 1

HCID 19923023HCID 19923023, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.6 g (0.039 mol) of cyclopropylamine hydrochloride are added to a solution of 3.9 g (0.03 mol) of ethyl acetoacetate and 8.16 g (0.03 mol) of methyl 2-(4-trifluoromethylbenzylidene)acetoacetate in 50 ml of pyridine and the mixture is heated under reflux for 5 hours. The reaction product is concentrated in vacuo, the residue is taken up in methylene chloride and water, the aqueous phase is separated off, and the methylene chloride solution is dried over sodium sulphate and evaporated. The residue is purified by chromatography on silica gel using methylene chloride as the solvent. After dissolving and crystallizing the product from n-heptane, 2.2 g (17.3% of theory) are obtained. Melting point: 110° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe reaction product is concentrated in vacuo
  4. customwater, the aqueous phase is separated off
  5. dry with materialthe methylene chloride solution is dried over sodium sulphate
  6. customevaporated
  7. customThe residue is purified by chromatography on silica gel
  8. dissolutionAfter dissolving
  9. customcrystallizing the product from n-heptane, 2.2 g (17.3% of theory)
  10. customare obtained

Sources & evidence

ORD record
ord-660ceefd099e407381cda19f0ae5e00d
Source dataset
uspto-grants-1993_08
Patent number
US05234935

Reaction notes

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