Methanol → HCID 53661416, compound

HRID 619114Notes

Reaction equation

HRID 619114 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[C:11](=O)[CH:10]=[C:9]2[CH2:18][C:19]([OH:21])=[O:20].[CH3:22]O>ClCCl>[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[CH2:11][CH:10]=[C:9]2[CH2:18][C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 15391206HCID 15391206, compound

Product 1

HCID 53661416HCID 53661416, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11 ml (147 mmol) of thionyl chloride are added dropwise over approximately 30 minutes to a stirred suspension of 12.5 g (49 mmol) of 6-chloro-1-methyl-2-oxo-1,2-dihydro-4-quinolineacetic acid in 150 ml of methanol. The mixture is stirred for 17 hours at room temperature and the solvent is driven off under vacuum. The residue is dissolved in 400 ml of dichloromethane, and then washed with saturated aqueous sodium bicarbonate solution and then with water. After drying over sodium sulphate, the organic phase is filtered and the filtrate is condensed. 11.16 g of expected product are obtained.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. dry with materialAfter drying over sodium sulphate
  3. filtrationthe organic phase is filtered
  4. customcondensed

Sources & evidence

ORD record
ord-5c7f564bde9d478b887271d6232c6c26
Source dataset
uspto-grants-1999_09
Patent number
US05958924

Reaction notes

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