Sodium Carbonate → HCID 19004323, compound

HRID 2225825Notes

Reaction equation

HRID 2225825 reaction equation
C([O:3][C:4](=[O:32])[C:5](=[O:31])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]2=3)=[CH:8][CH:7]=1)C.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[O:30]=[C:29]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:16]1[CH2:15][CH2:14][CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([C:5](=[O:31])[C:4]([OH:32])=[O:3])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 54227746HCID 54227746, compound

Product 1

HCID 19004323HCID 19004323, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-[3-(5,6-dihydro-6-oxo-5-phenanthridinyl)propoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.4 g) in hot methanol (80 mL) was treated with sodium carbonate (0.118 g) in water (1.5 mL), and the reaction was stirred at room temperature for 4 hours. After the methanol was removed in vacuo, dichloromethane and water were added and the mixture was acidified with 3N hydrochloric acid. The resulting solid was filtered off, dried and crystallized from ethyl acetate-tetrahydrofuran to yield 0.321 g of 4-[3-(5,6-dihydro-6-oxo-5-phenanthridinyl)propoxy]-alpha-oxobenzeneacetic acid in two crops, mp 202°-204° C.

Workup

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

Sources & evidence

ORD record
ord-1caa41a53fcc45f69fe045179cdc7592
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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