Sodium Hydroxide → 2-Amino-3-biphenylacetic Acid Hydrate

HRID 325319

Reaction equation

HRID 325319 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:15]=2[NH:14][C:13](=[O:16])[CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:17].[Na+]>>[OH2:16].[NH2:14][C:15]1[C:11]([CH2:12][C:13]([OH:16])=[O:17])=[CH:10][CH:9]=[CH:8][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 133019777-phenyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 133019802-Amino-3-biphenylacetic Acid Hydrate

Procedure

A mixture of 4.5 g. (0.0215 mole) of 7-phenylindolin-2-one and 60 ml. of 3 N sodium hydroxide was heated at reflux under nitrogen for 17 hrs. The reaction mixture was cooled, filtered, and the filtrate was diluted with 60 ml. of water. The solution was cooled, made acidic with glacial acetic acid and the resulting tan solid was immediately collected by filtration, washed with cold water and dried under vacuum to yield 4.6 g. (98%) of product as a tan solid, m.p. 98°-100° C. (dec.).

Workup

  1. additionA mixture of 4.5 g
  2. temperatureat reflux under nitrogen for 17 hrs
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. additionthe filtrate was diluted with 60 ml
  6. temperatureThe solution was cooled
  7. filtrationthe resulting tan solid was immediately collected by filtration
  8. washwashed with cold water
  9. customdried under vacuum
  10. customto yield 4.6 g

Sources & evidence

ORD record
ord-dc63a2a4863f4abc8c644aff0c8f8237
Source dataset
uspto-grants-1984_04
Patent number
US04440785

Linked notes

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