Hydrazine hydrate (1:1) → 4-(Hydroxymethyl)benzohydrazide

HRID 44228

Reaction equation

HRID 44228 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][CH:4]=1.O.[NH2:14][NH2:15]>C(O)C>[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:14][NH2:15])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 81325Methyl 4-(hydroxymethyl)benzoate

Product 1

HCID 432368204-(Hydroxymethyl)benzohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 4-(hydroxymethyl)benzoate (6.6 g, 40 mmol) and hydrazine hydrate (6 mL) in ethanol (30 mL) was stirred at reflux for 20 hours. The reaction mixture was concentrated to half volume through atmospheric pressure distillation. The solid was collected by filtration and washed with cold ethanol (2×10 mL). The filtrate was further concentrated and a second crop was similarly obtained and combined. The 4-(hydroxymethyl)benzohydrazide was obtained as a white solid (6.1 g, 93%). 400 MHz 1H NMR (DMSO-d6) δ: 9.68 (s, 1H), 7.75 (dd, J=6.4, 1.6 Hz, 2H), 7.34 (d, J=8.0 Hz, 2H), 5.25 (t, J=6.0 Hz, 1H), 4.50 (d, J=6.0 Hz, 2H), 4.43 (s, 2H).

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationThe reaction mixture was concentrated to half volume through atmospheric pressure distillation
  3. filtrationThe solid was collected by filtration
  4. washwashed with cold ethanol (2×10 mL)
  5. concentrationThe filtrate was further concentrated
  6. customa second crop was similarly obtained

Sources & evidence

ORD record
ord-0c0fc23b09684c52baf772134855872e
Source dataset
uspto-grants-2013_09
Patent number
US08541407B2

Linked notes

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