Lithium Hydroxide → (4-Fluoroanilino)acetic acid

HRID 1507635Notes

Reaction equation

HRID 1507635 reaction equation
C([N:3]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH2:4][C:5]([OH:7])=[O:6])C.[Li+].[OH-]>C1COCC1.O>[F:14][C:11]1[CH:10]=[CH:9][C:8]([NH:3][CH2:4][C:5]([OH:7])=[O:6])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 61998283ethyl N-(4-fluorophenyl)glycine

Product 1

HCID 1133296(4-Fluoroanilino)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 21.3 g (108 mmole) of ethyl N-(4-fluorophenyl)glycine in THF (100 mL) under nitrogen was added LiOH (5.44 g (130 mmol) monohydrate in 25 mL water. After 15 h the mixture was concentrated to half the volume and acidified to pH 3 with HCl. The precipitated solid was collected and washed with water (100 mL) to afford the title compound.

Workup

  1. concentrationAfter 15 h the mixture was concentrated to half the volume
  2. customThe precipitated solid was collected
  3. washwashed with water (100 mL)

Sources & evidence

ORD record
ord-29093dc73551402f8645b833fe1ed16d
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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