Water → HCID 620332, compound

HRID 1497167Notes

Reaction equation

HRID 1497167 reaction equation
C[O:2][C:3]([C:5]1[C:6](=[O:22])[NH:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)=[O:4].[OH-].[Li+].O>C(O)C>[Cl:21][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:22])[C:5]([C:3]([OH:4])=[O:2])=[C:14]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 15422727HCID 15422727, compound

Product 1

HCID 620332HCID 620332, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid methyl ester (380 mg, 1.21 mmol, Eq: 1.00) and lithium hydroxide (3.8 ml, 3.8 mmol, Eq: 3.14) in ethanol (7.6 ml) was heated to 50° C. for 72 h in a sealed tube. Then water was added and the mixture was extracted with diethylether (3×). The pH of the aqueous layer was then adjusted to 1 by addition of 1N HCl and the mixture was extracted with ethyl acetate (3×). The combined ethyl acetate extracts were washed with brine, dried with Na2SO4 and evaporated to yield the title compound (378 mg) as off-white solid. MS (ESI): 300.0 (M+H)+.

Workup

  1. extractionthe mixture was extracted with diethylether (3×)
  2. additionThe pH of the aqueous layer was then adjusted to 1 by addition of 1N HCl
  3. extractionthe mixture was extracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate extracts were washed with brine
  5. dry with materialdried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-b94e09519dc44ba3b4df43f9ede251bd
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

Loading…