Hydrochloric Acid → HCID 21268852, compound

HRID 1194845Notes

Reaction equation

HRID 1194845 reaction equation
Cl[C:2]1[C:15]([OH:16])=[CH:14][C:13]2[O:12][C:11]3[C:6](=[C:7]([F:17])[CH:8]=[CH:9][CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].Br[CH2:24][C:25]([O:27]CC)=[O:26].[OH-].[Na+].[ClH:32]>O.CN(C=O)C>[Cl:32][CH:24]([O:16][C:15]1[CH:2]=[CH:3][C:4]2[C:5](=[O:18])[C:6]3[C:11]([O:12][C:13]=2[CH:14]=1)=[CH:10][CH:9]=[CH:8][C:7]=3[F:17])[C:25]([OH:27])=[O:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 19660Carbonate IonHCID 15617003HCID 15617003, compound

Product 1

HCID 21268852HCID 21268852, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.3 g of 2-chloro-8-fluoro-3-hydroxy-9-oxo-9H-xanthene, 1.7 g of postassium carbonate, 2.1 g of ethyl bromoacetate and 30 ml of DMF was stirred at 60°-65° C. for 3 hours. After cooling the mixture, 2 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 DMF gave 1.0 g of 2-chloro-8-fluoro-9-oxo-9H-xanthene-3-yloxyacetic acid. m.p. 239°-242° C. This compound gave 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 DMF

Sources & evidence

ORD record
ord-fbe5246ebfea4f6b88e49771afe3908a
Source dataset
uspto-grants-1989_03
Patent number
US04816479

Reaction notes

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