Hydrochloric Acid → (2-Amino-5-benzoylphenyl)acetic acid

HRID 1704327Notes

Reaction equation

HRID 1704327 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:19].[Na+].Cl>>[NH2:14][C:15]1[CH:16]=[CH:17][C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][C:11]=1[CH2:12][C:13]([OH:18])=[O:19]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 134081645-Benzoyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 13408170(2-Amino-5-benzoylphenyl)acetic acid

Procedure

A mixture of 1.0 g. (0.004 mole) of 5-benzoylindolin-2-one and 30 ml. of 3N sodium hydroxide was refluxed for 0.5 hour. The reaction mixture was cooled, acidified to pH 6 with 3N hydrochloric acid and slightly acidic solution was extracted with chloroform. The chloroform extracts were dried (magnesium sulfate) and concentrated to a solid. Recrystallization from ethanol-water gave 0.9 g. (84.5%) of pure product which melted at 143°-145° C.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureThe reaction mixture was cooled
  3. extractionwas extracted with chloroform
  4. dry with materialThe chloroform extracts were dried (magnesium sulfate)
  5. concentrationconcentrated to a solid
  6. customRecrystallization from ethanol-water
  7. customgave 0.9 g

Sources & evidence

ORD record
ord-8fb5fd6027334b1b979cd4a72a7d7613
Source dataset
uspto-grants-1978_11
Patent number
US04126635

Reaction notes

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