Dimedone → Propan-2-yl 4-(2,3-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

HRID 636537Notes

Reaction equation

HRID 636537 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]1([CH3:20])[CH2:19][C:17](=O)[CH2:16][C:14](=[O:15])[CH2:13]1.[NH2:21]/[C:22](/[CH3:30])=[CH:23]\[C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25]>C(O)(C)C>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:16]2[C:14](=[O:15])[CH2:13][C:12]([CH3:11])([CH3:20])[CH2:19][C:17]=2[NH:21][C:22]([CH3:30])=[C:23]1[C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 31358DimedoneHCID 357452,3-DichlorobenzaldehydeHCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl ester

Product 1

HCID 2847332Propan-2-yl 4-(2,3-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3.50 g (20 mmol) of 2,3-dichlorobenzaldehyde, 2.80 g (20 mmol) of dimedone and 2.86 g (20 mmol) of isopropyl 3-aminocrotonate are dissolved in 100 ml of isopropanol and stirred under reflux for 5 h. The product precipitates. The mixture is treated with 50 ml of water and cooled to RT. The product is filtered off with suction and washed successively with isopropanol, ethanol and ether. 6.6 g (78% of theory) of the title compound are obtained.

Workup

  1. temperatureunder reflux for 5 h
  2. customThe product precipitates
  3. additionThe mixture is treated with 50 ml of water
  4. filtrationThe product is filtered off with suction
  5. washwashed successively with isopropanol, ethanol and ether

Sources & evidence

ORD record
ord-6c3d3caf700a4c539dc0fe0b6d63dcfd
Source dataset
uspto-grants-2001_02
Patent number
US06194428B1

Reaction notes

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