Sodium Hydroxide → HCID 13537754, compound

HRID 1583944Notes

Reaction equation

HRID 1583944 reaction equation
[C:1]([CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:9][C:8]=1[Cl:19])([OH:3])=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:19][C:8]1[CH:9]=[C:10]([CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:11]=[C:12]2[C:7]=1[NH:6][CH2:5][CH2:4][C:1]2=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13537753HCID 13537753, compound

Product 1

HCID 13537754HCID 13537754, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Further, the suspension of 80 g of polyphosphoric acid and 80 ml of toluene was stirred at 100° C., 20 ml of toluene solution of above-mentioned compound (methyl 2-[4-(2-carboxyethylamino)-3-chlorophenyl]propionate) were added thereto and stirred for further 1 hour. After cooling, ice-water was added to the reaction mixture, then the mixture was poured into an aqueous solution of sodium hydroxide to adjust the pH to 9 to 10, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was subjected to column chromatography on silica gel, eluted with a mixture of ether and hexane to give 6.4 g of methyl 2-(8-chloro-1,2,3,4-tetrahydro-4-oxoquinolin-6-yl)propionate (Compound 32).

Workup

  1. stirringstirred for further 1 hour
  2. temperatureAfter cooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. washeluted with a mixture of ether and hexane

Sources & evidence

ORD record
ord-4c3f6478250949da9bfa436d823abd7a
Source dataset
uspto-grants-1985_11
Patent number
US04555513

Reaction notes

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