Acetic Acid → 4-[Amino(carboxy)methyl]-3-methylbenzoic acid

HRID 343923Notes

Reaction equation

HRID 343923 reaction equation
C(C1[CH:8]=[CH:7][C:6]([CH:9]2[NH:13]C(=O)N[C:10]2=[O:15])=[C:5]([CH3:16])[CH:4]=1)#N.[C:17]([OH:20])(=[O:19])[CH3:18].[OH-:21].[Na+]>>[C:17]([C:18]1[CH:8]=[CH:7][C:6]([CH:9]([C:10]([OH:15])=[O:21])[NH2:13])=[C:5]([CH3:16])[CH:4]=1)([OH:20])=[O:19]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 118060795-(4-Cyano-2-methylphenyl)hydantoin

Product 1

HCID 39317054-[Amino(carboxy)methyl]-3-methylbenzoic acid

Procedure

A stirred mixture of 5-(4-cyano-2-methylphenyl)hydantoin (1.1 g, 5.2 mmol) in aqueous sodium hydroxide (2M, 12 ml) was heated to 120° C. for 17 hours in a PTFE lined stainless steel sealed reaction vessel. The cooled mixture was acidified with glacial acetic acid (1.4 ml) and chromatographed on ion exchange (Dowex 50×8-100 resin). The column was eluted sequentially with water, tetrahydrofuran-water (1:1), water and 10% pyridine in water. Fractions collected from the pyridine-water elution were combined and evaporated to dryness, redissolved in water and freeze-dried to give the title compound as a white powder, m.p. >250° C.

Workup

  1. customsealed
  2. customreaction vessel
  3. customchromatographed on ion exchange (Dowex 50×8-100 resin)
  4. washThe column was eluted sequentially with water, tetrahydrofuran-water (1:1), water and 10% pyridine in water
  5. customFractions collected from the pyridine-water elution
  6. customevaporated to dryness
  7. dissolutionredissolved in water
  8. customfreeze-dried

Sources & evidence

ORD record
ord-2ffe9c2e79ad4e378e6b81c9d45fcb2f
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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