Methanol → HCID 20257366, compound

HRID 1583943Notes

Reaction equation

HRID 1583943 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9]([CH3:13])([CH3:12])[CH:8]=[CH:7]2.CO.C(=O)([O-])[O-:23].[K+].[K+]>[Pd](Cl)Cl.C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9]([CH3:12])([CH3:13])[CH2:8][C:7]2=[O:23]

Participants

6

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 20257399HCID 20257399, compound

Product 1

HCID 20257366HCID 20257366, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 241BenzeneSolvent

Procedure

1.0 g of methyl 2-(8-chloro-1,2-dihydro-2,2-dimethylquinolin-6-yl)propionate was added to 20 ml of methanol. 2.0 g of palladium chloride was further added to the solution, and the mixture was stirred at 55°-60° C. for 6 hours. After cooling, 2 g of potassium carbonate and benzene were added to the mixture, then the mixture was further stirred. The precipitates were filtered off and washed with benzene. The filtrate and the wash were combined and concentrated, followed by addition of dilute aqueous solution of sodium hydrogencarbonate, and extraction with ether. The ethereal solution was washed with water, saturated aqueous solution of sodium sulfate and then the solvent was distilled off. The residue was purified by column chromatography on silica gel (benzene:ether=9:1) to give 0.3 g of methyl 2-(8-chloro-1,2,3,4-tetrahydro-2,2-dimethyl-4-oxoquinolin-6-yl)propionate (Compound 31).

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitates were filtered off
  3. washwashed with benzene
  4. concentrationconcentrated
  5. additionfollowed by addition of dilute aqueous solution of sodium hydrogencarbonate, and extraction with ether
  6. washThe ethereal solution was washed with water, saturated aqueous solution of sodium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by column chromatography on silica gel (benzene:ether=9:1)

Sources & evidence

ORD record
ord-56822bad7e5e4ad2a868591226fa2999
Source dataset
uspto-grants-1985_11
Patent number
US04555513

Reaction notes

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