Hydrazine hydrate (1:1) → 3-bromo-4-methylbenzohydrazide

HRID 1754325Notes

Reaction equation

HRID 1754325 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([Br:11])[CH:5]=1.O.[NH2:14][NH2:15]>CO>[Br:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[CH3:10])[C:3]([NH:14][NH2:15])=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 7015747Methyl 3-bromo-4-methylbenzoate

Product 1

HCID 13828763-bromo-4-methylbenzohydrazideYield 50.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl-3-bromo-4-methylbenzoate (5.0 g, 21.8 mmol, 1.0 eq) and hydrazine hydrate (5 mL, 99 mmol, 4.5 eq) in methanol (50 mL) was heated to 80° C. overnight. The reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated under vacuum. The residue was taken in ethyl acetate (100 mL) and washed with water (2×50 mL), brine (50 mL), dried (Na2SO4) and filtered. The filtrate was evaporated under reduced pressure to afford 2.5 g (50%) of the desired product as a white solid. 1HNMR (400 MHz, DMSO-d6) δ 9.84 (s, 1H, D2O exchangeable), 8.02 (d, J=1.0 Hz, 1H), 7.74 (dd, J=1.0, 8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 3.35 (s, 2H, D2O exchangeable), 2.38 (s, 3H); ESI-MS (m/z) 229, 231 [(MH)+, Br79,81].

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated under vacuum
  4. washwashed with water (2×50 mL), brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-63b63b06cd5b4093b70d13d731eea1d5
Source dataset
uspto-grants-2015_10
Patent number
US09169242B2

Reaction notes

Loading…