HCID 57582493, compound → HCID 15980989, compound

HRID 1692166Notes

Reaction equation

HRID 1692166 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([O:15][CH2:16][CH3:17])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)(=O)C>O.NN>[CH2:16]([O:15][CH:11]([C:8]1[CH:7]=[CH:6][C:5]([NH2:4])=[CH:10][CH:9]=1)[C:12]([OH:14])=[O:13])[CH3:17]

Participants

3

Reactant 1

HCID 57582493HCID 57582493, compound

Product 1

HCID 15980989HCID 15980989, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

2-(4-Acetamidophenyl)-2-ethoxyacetic acid (7.54 g, 31.8 mmol) was heated with hydrazine monohydrate (40 ml) for 16 hr, the mixture cooled then concentrated in vacuo. The residual oil was then purified by silica column chromatography (20-40% methanol in CH2Cl2 eluent) to give (±)-2-ethoxy-2-(4′-aminophenyl)-acetic acid (2.3 g, 37%) as a white foam.

Workup

  1. temperaturethe mixture cooled
  2. concentrationthen concentrated in vacuo
  3. customThe residual oil was then purified by silica column chromatography (20-40% methanol in CH2Cl2 eluent)

Sources & evidence

ORD record
ord-7384d1c77d9244e297b1afc04925f645
Source dataset
uspto-grants-2012_04
Patent number
US08153841B2

Reaction notes

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