Hydrazine → 2-(4-Hydroxyphenyl)acetohydrazide

HRID 1921615Notes

Reaction equation

HRID 1921615 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[NH2:13][NH2:14]>CO>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([NH:13][NH2:14])=[O:2])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 37318662-(4-Hydroxyphenyl)acetohydrazideYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (4-Hydroxy-phenyl)-acetic acid methyl ester (5 g, 30.08 mmol) in MeOH (20 mL, anhydrous) was added hydrazine (3.77 mL, 120.35 mmol) and then heated to 55° C. for 1 hour. A white precipitate formed during heating. The reaction was then cooled to rt and stirred for an additional hour to facilitate precipitation of solid. The reaction was filtered and the solid was washed with MeOH and dried resulting in the desired product (4.3 g, 86%) as a white solid. 1H-NMR (DMSO): δ 9.20 (1H, s), 9.10 (1H, s), 7.04-7.02 (2H, d, J=8.6 Hz), 6.67-6.65 (2H, d, J=8.6 Hz), 4.17-4.16 (2H, s), 4.11-4.09 (1H, q, J=5.0, 5.5 Hz).

Workup

  1. customA white precipitate formed
  2. temperatureduring heating
  3. temperatureThe reaction was then cooled to rt
  4. customprecipitation of solid
  5. filtrationThe reaction was filtered
  6. washthe solid was washed with MeOH
  7. customdried

Sources & evidence

ORD record
ord-ad93197015284dd3adf908a4a042859d
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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