Hydrochloric Acid → HCID 13669834, compound

HRID 1194846Notes

Reaction equation

HRID 1194846 reaction equation
[Cl:1][C:2]1[C:3]([OH:18])=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][C:8]=3[F:16].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29]CC)=[O:28].[OH-].[Na+].Cl>O.CN(C=O)C>[Cl:1][C:2]1[C:3]([O:18][CH2:26][C:27]([OH:29])=[O:28])=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][C:8]=3[F:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 15617014HCID 15617014, compound

Product 1

HCID 13669834HCID 13669834, compoundYield 37.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.6 g of 3-chloro-8-fluoro-2-hydroxy-9-oxo-9H-xanthene, 3.4 g of potassium carbonate, 4.2 g of ethyl bromoacetate and 60 ml of DMF was stirred at 60°-65° C. for 5 hours. After cooling the mixture, 4 g of sodium hydroxide and 100 ml of water were added and the resulting mixture was stirred at 90°-100° C. for 30 minutes. After cooling, the mixture was rendered acidic with hydrochloric acid and the solid crystal was recovered by filtration, washed with water and dried. Recrystallization from ethanol gave 1.2 g of 3-chloro-8-fluoro-9-oxo-9H-xanthene-2-yloxyacetic acid. m.p. 242°-245° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 322.

Workup

  1. additionwere added
  2. stirringthe resulting mixture was stirred at 90°-100° C. for 30 minutes
  3. temperatureAfter cooling
  4. filtrationthe solid crystal was recovered by filtration
  5. washwashed with water
  6. customdried
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-0f6a7b57144b4936a803202e01c18f61
Source dataset
uspto-grants-1989_03
Patent number
US04816479

Reaction notes

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