Methyl acetoacetate → 4-Methyl-7-(thiophen-3-yl)-1,2,5,6,7,8-hexahydroquinoline-2,5-dione

HRID 1700649Notes

Reaction equation

HRID 1700649 reaction equation
[NH2:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[CH2:5][C:4](=[O:13])[CH:3]=1.[C:14](OC)(=[O:19])[CH2:15][C:16]([CH3:18])=O>C(OCC)(=O)C>[CH3:18][C:16]1[C:3]2[C:4](=[O:13])[CH2:5][CH:6]([C:8]3[CH:12]=[CH:11][S:10][CH:9]=3)[CH2:7][C:2]=2[NH:1][C:14](=[O:19])[CH:15]=1

Participants

4

Reactant 2

HCID 7757Methyl acetoacetateHCID 183175081-Amino-5-(3-thienyl)cyclohexen-3-one

Product 1

HCID 183175574-Methyl-7-(thiophen-3-yl)-1,2,5,6,7,8-hexahydroquinoline-2,5-dioneYield 22%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 1-amino-5-(thiophen-3-yl)cyclohexen-3-one (4.75 g) and methyl acetoacetate (10 g) was stirred at 170° C. for 18 hours and cooled, and to the mixture was added ethyl acetate. Precipitated crystals were filtered and washed with ethyl acetate to give 4-methyl-7-(thiophen-3-yl)-1,2,5,6,7,8-hexahydroquinoline-2,5-dione (1.4 g) as yellow crystals.

Workup

  1. temperaturecooled
  2. customPrecipitated crystals
  3. filtrationwere filtered
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-00e072b0c1ba4d299b7579ece82677b5
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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