Ethyl bromoacetate → HCID 13590327, compound

HRID 1380100Notes

Reaction equation

HRID 1380100 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:12])[C:10]=1[Cl:11])[C:7](=[O:13])[C:6]([CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)([CH3:14])[CH2:5]2.C(=O)([O-])[O-].Br[CH2:25][C:26]([O:28]CC)=[O:27]>CC(C)=O>[Cl:11][C:10]1[C:9]([Cl:12])=[C:8]2[C:4]([CH2:5][C:6]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)([CH3:14])[C:7]2=[O:13])=[CH:3][C:2]=1[NH:1][CH2:25][C:26]([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 19660Carbonate IonHCID 13590326HCID 13590326, compound

Product 1

HCID 13590327HCID 13590327, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-amino-6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1H-inden-1-one (800 mg), postassium carbonate (440 mg), and ethyl bromoacetate (540 mg) in acetone (20 ml) is heated at reflux overnight. The reaction mixture is filtered, the acetone is distilled at reduced pressure and the residual oil is dissolved in a mixture of ethanol (5 ml) and methylene chloride (5 ml) and treated with 10 N sodium hydroxide (2 ml). The mixture is stirred overnight, the solvents are distilled at reduced pressure and the residue is treated with water, then filtered and acidified with hydrochloric acid and extracted with ethyl acetate. Evaporation of the ethyl acetate gives 150 mg of [(6,7-dichloro-2-cyclo-pentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)amino]acetic acid which melts at 199°-200° C. after recrystallization from chloroform-hexane.

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture is filtered
  4. distillationthe acetone is distilled at reduced pressure
  5. dissolutionthe residual oil is dissolved in a mixture of ethanol (5 ml) and methylene chloride (5 ml)
  6. additiontreated with 10 N sodium hydroxide (2 ml)
  7. distillationthe solvents are distilled at reduced pressure
  8. additionthe residue is treated with water
  9. filtrationfiltered
  10. extractionextracted with ethyl acetate
  11. customEvaporation of the ethyl acetate

Sources & evidence

ORD record
ord-f7c128b9cf1e4c2cba6dc35946ed86fe
Source dataset
uspto-grants-1986_04
Patent number
US04579869

Reaction notes

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