Sodium Carbonate → HCID 19004340, compound

HRID 2225827Notes

Reaction equation

HRID 2225827 reaction equation
C([O:3][C:4](=[O:28])[C:5](=[O:27])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]2=[O:26])=[CH:8][CH:7]=1)C.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[O:26]=[C:17]1[CH:18]=[CH:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:16]1[CH2:15][CH2:14][CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([C:5](=[O:27])[C:4]([OH:28])=[O:3])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 54247125HCID 54247125, compound

Product 1

HCID 19004340HCID 19004340, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-[3-(1,2-dihydro-2-oxo-1-quinolinyl)propoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.5 g) in hot methanol (50 mL) was treated with sodium carbonate (0.14 g) in water (1.5 mL), and the reaction was stirred at room temperature for 5 hours. After the methanol was removed in vacuo, dichloromethane and water were added and the rnixmre was acidified with 3N hydrochloric acid. The precipitated solid was faltered off, dried and then crystallized from ethyl acetate-tetrahydrofuran to afford 0.337 g of 4-[3-(1,2-dihydro-2-oxo-1-quinolinyl)propoxy]-alpha-oxobenzeneacetic acid, mp 183°-186° C.

Workup

  1. customAfter the methanol was removed in vacuo, dichloromethane and water
  2. additionwere added
  3. customdried
  4. customcrystallized from ethyl acetate-tetrahydrofuran

Sources & evidence

ORD record
ord-0a8aa936ab14448cb75f58189697f2cc
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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