Pyridine → HCID 20257372, compound

HRID 1583942Notes

Reaction equation

HRID 1583942 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:12]([CH3:17])[C:13]([O:15][CH3:16])=[O:14])[CH:8]=2)[NH:3]1.N1C=CC=CC=1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CCOCC>[C:25]([N:3]1[C:4]2[C:9](=[CH:8][C:7]([CH:12]([CH3:17])[C:13]([O:15][CH3:16])=[O:14])=[CH:6][CH:5]=2)[CH2:10][CH2:11][C:2]1([CH3:18])[CH3:1])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 20257377HCID 20257377, compound2×

Product 1

HCID 20257372HCID 20257372, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.0 g of methyl 2-(1,2,3,4-tetrahydro-2,2-dimethylquinolin-6-yl)propionate (Compound 11) were added to 30 ml of pyridine, and 2.6 g of benzoyl chloride was further added to the solution. The mixture was stirred at room temperature for 15 hours, followed by addition of ice-water and extraction with ether. The ethereal solution was washed with 10% hydrochloric acid, water and saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. Ether was distilled off to give 3.9 g of methyl 2-(1-benzoyl-1,2,3,4-tetrahydro-2,2-dimethylquinolin-6-yl)propionate (Compound 17).

Workup

  1. additionwas further added to the solution
  2. washThe ethereal solution was washed with 10% hydrochloric acid, water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationEther was distilled off

Sources & evidence

ORD record
ord-fdcca4984ba74eadb1cae7e1727d1da7
Source dataset
uspto-grants-1985_11
Patent number
US04555513

Reaction notes

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