HCID 57582496, compound → HCID 15980988, compound

HRID 2370467Notes

Reaction equation

HRID 2370467 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([O:15][CH3:16])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)(=O)C>O.NN>[CH3:16][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]

Participants

3

Reactant 1

HCID 57582496HCID 57582496, compound

Product 1

HCID 15980988HCID 15980988, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

2-(4-Acetamidophenyl)-2-methoxyacetic acid (7.1 g, 31.8 mmol) was heated with hydrazine monohydrate (40 ml) for 16 hr, cooled and concentrated in vacuo. The resulting residual oil was purified by silica gel column chromatography (eluent 20-40% methanol in CH2Cl2) to give 2.6 g (45%) of (±)-2-methoxy-2-(4′-aminophenyl)-acetic acid 1H NMR (δ, 250 MHz, CD3OD): 3.27 (3H, s), 4.43 (1H, s), 6.66 (2H, d, 8.5 Hz), 7.18 (2H, d, 8.2 Hz).

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. customThe resulting residual oil was purified by silica gel column chromatography (eluent 20-40% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-680b3baf2cf94db4b3bba44b2f668ef7
Source dataset
uspto-grants-2014_04
Patent number
US08710100B2

Reaction notes

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