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

HRID 636536Notes

Reaction equation

HRID 636536 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH:11]1([CH:18]=[CH:17][CH:16]=[C:14]([OH:15])[CH2:13]1)O.[NH2:19]/[C:20](/[CH3:28])=[CH:21]\[C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23]>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:13]2[C:14](=[O:15])[CH2:16][CH2:17][CH2:18][C:11]=2[NH:19][C:20]([CH3:28])=[C:21]1[C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl esterHCID 19922823Cyclohexa-3,5-diene-1,3-diol

Product 1

HCID 2847040Propan-2-yl 4-(2,3-dichlorophenyl)-2-methyl-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, 2.24 g (20 mmol) of dihydroresorcinol 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. 5.8 g (74% 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-a0fa06fea45c46718f7d1b60eac63f03
Source dataset
uspto-grants-2001_02
Patent number
US06194428B1

Reaction notes

Loading…