Methyl acetoacetate → HCID 18317534, compound

HRID 1700651Notes

Reaction equation

HRID 1700651 reaction equation
[NH2:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[CH2:5][C:4](=[O:15])[CH:3]=1.[C:16](OC)(=[O:21])[CH2:17][C:18]([CH3:20])=O>>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH:6]1[CH2:7][C:2]2[NH:1][C:16](=[O:21])[CH:17]=[C:18]([CH3:20])[C:3]=2[C:4](=[O:15])[CH2:5]1

Participants

3

Reactant 2

HCID 7757Methyl acetoacetate2×HCID 98593161-Amino-5-(2-chlorophenyl)cyclohexen-3-one

Product 1

HCID 18317534HCID 18317534, compoundYield 4.9%

Conditions

Temperature
170 °C

Procedure

A mixture of 1-amino-5-(2-chlorophenyl)cyclohexen-3-one (6.66 g) and methyl acetoacetate (5.8 g) was stirred at 170° C. for 2.5 hours, and to the mixture was added methyl acetoacetate (3 g). The mixture was stirred for 1.5 hours and cooled, and precipitated crystals were filtered and washed with ethanol to give 7-(2-chlorophenyl)-4-methyl-1,2,5,6,7,8-hexahydroquinoline-2,5-dione (0.42 g) as pale yellow crystals.

Workup

  1. stirringThe mixture was stirred for 1.5 hours
  2. temperaturecooled
  3. customprecipitated crystals
  4. filtrationwere filtered
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-9ec7615d9b614d18b14aa57a66bd2714
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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