Anthranilic Acid → HCID 3619576, compound

HRID 262382Notes

Reaction equation

HRID 262382 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(=O)([O-])[O-].[Na+].[Na+].Br[CH:18]1[CH2:23][CH2:22][O:21][C:19]1=[O:20].Cl>O>[C:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH:18]1[CH2:23][CH2:22][O:21][C:19]1=[O:20])([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 954632(3H)-Furanone, 3-bromodihydro-

Product 1

HCID 3619576HCID 3619576, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 68.6 g of anthranilic acid, 132.2 g of sodium carbonate and 400 ml of water was stirred at room temperature for 1 hour and, under ice-cooling, 103.2 g of α-bromo-γ-butyrolactone was added dropwise. The mixture was stirred under ice-cooling for 5 hours and, then, at room temperature for 24 hours. The mixture was made acidic with hydrochloric acid, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. The ethyl acetate was distilled off and ethyl ether was added to the residue. The resulting crystals were recovered by filtration. By the above procedure was obtained α-[(2-carboxyphenyl)amino]-γ-butyrolactone, melting point: 197°-198° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred under ice-
  3. temperaturecooling for 5 hours
  4. waitat room temperature for 24 hours
  5. extractionextracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationThe ethyl acetate was distilled off
  9. additionethyl ether was added to the residue
  10. filtrationThe resulting crystals were recovered by filtration

Sources & evidence

ORD record
ord-165442e226a14dd0b6d752955dbf630f
Source dataset
uspto-grants-1979_05
Patent number
US04154731

Reaction notes

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