Water → 2-(4-Hydroxyphenyl)acetohydrazide

HRID 1822888Notes

Reaction equation

HRID 1822888 reaction equation
[NH2:1][NH2:2].C[O:4][C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.O>CO>[OH:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C:5]([NH:1][NH2:2])=[O:4])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 37318662-(4-Hydroxyphenyl)acetohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
52.5 °C

Procedure

Neat anhydrous hydrazine 21.0 g (654 mmol) was added to a solution of p-hydroxyphenylacetic acid methyl ester 27.18 g (163.5 mmol) in MeOH (100 mL) and the mixture was heated to 50-55° C. and stirred at this temperature for 90 min (water bath). Cooled, stirred for extra 1 hour, the precipitate collected by filtration, compressed on the frit, washed with MeOH (3×10 mL) and dried on high vacuum. A second fraction was obtained by cooling the supernatants to −15° C. overnight and filtering the formed precipitate.

Workup

  1. temperatureCooled
  2. filtrationthe precipitate collected by filtration
  3. washwashed with MeOH (3×10 mL)
  4. customdried on high vacuum
  5. customA second fraction was obtained
  6. temperatureby cooling the supernatants to −15° C. overnight
  7. filtrationfiltering the formed precipitate

Sources & evidence

ORD record
ord-301600a6e63b4080a3dd472f88e8fa4b
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Reaction notes

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