Hydrazine hydrate (1:1) → 3-(3-Trifluoromethylbenzamido)benzhydrazide

HRID 970272Notes

Reaction equation

HRID 970272 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12](OC)=[O:13])=[O:7].O.[NH2:25][NH2:26]>O1CCCC1>[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([NH:25][NH2:26])=[O:13])=[O:7]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 850566Methyl 3-(3-trifluoromethylbenzamido)benzoate

Product 1

HCID 694126823-(3-Trifluoromethylbenzamido)benzhydrazideYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.0 gm (3.09 mmol) of methyl 3-(3-trifluoromethylbenzamido)benzoate in 19 mL of tetrahydrofuran was added 1.06 mL (30.9 mmol) of hydrazine hydrate. The reaction was heated to reflux for 48 hr. After cooling, the reaction mixture was concentrated under rotevaporation, and ether and water were added. The solid product was separated by filtration and dried in vacuo to give 785 mg (2.43 mmol, 79% yield) of 3-(3-trifluoromethylbenzamido)benzhydrazide as a white solid. MS m/z: 324.0 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 48 hr
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under rotevaporation, and ether and water
  5. additionwere added
  6. customThe solid product was separated by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-39dd6924c0bb48c6aa397625a13fbac9
Source dataset
uspto-grants-2007_12
Patent number
US07312181B2

Reaction notes

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