Sodium Hydroxide → 3-[(4-Bromo-2-methylphenyl)amino]-3-oxopropanoic acid

HRID 486984Notes

Reaction equation

HRID 486984 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][C:11]([O:13]CC)=[O:12])=[C:4]([CH3:17])[CH:3]=1.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][C:11]([OH:13])=[O:12])=[C:4]([CH3:17])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14150214Ethyl 3-[(4-bromo-2-methylphenyl)amino]-3-oxopropanoate

Product 1

HCID 129348693-[(4-Bromo-2-methylphenyl)amino]-3-oxopropanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 6.0 gram (0.02 mole) portion of ethyl 3-[(4-bromo-2-methylphenyl)amino]-3-oxopropanoate prepared in Example I (Compound No. 75) was dissolved in approximately 80 milliliters of ethanol and 1.2 grams (0.03 mole) of sodium hydroxide pellets were added to the resulting mixture. The mixture was stirred for four hours and then allowed to stand overnight. The mixture was then evaporated to dryness and water added to give a yellow cloudy solution. This solution was extracted with methylene chloride and then acidified with 10% hydrochloric acid causing a white precipitate to form. The white precipitate was worked up to give 1.8 grams (0.01 mole) of 3-[(4-bromo-2-methylphenyl)amino]-3-oxopropanoic acid as a white solid having a melting point of 163° C.-165° C. Elemental analysis of the product indicated the following:

Workup

  1. waitto stand overnight
  2. customThe mixture was then evaporated to dryness and water
  3. additionadded
  4. customto give a yellow cloudy solution
  5. extractionThis solution was extracted with methylene chloride
  6. customto form

Sources & evidence

ORD record
ord-6582a6d3e16b4398b564688c68c1d4c1
Source dataset
uspto-grants-1994_03
Patent number
US05292937

Reaction notes

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