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

HRID 893192Notes

Reaction equation

HRID 893192 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.

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-8b0f69e659ad473891e687c7ab02f77b
Source dataset
uspto-grants-1992_06
Patent number
US05123951

Reaction notes

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