Methylhydrazine → 3-methyl-3H-benzo[d][1,2]diazepin-4(5H)-one

HRID 2302278Notes

Reaction equation

HRID 2302278 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=O)=O.[CH3:13][NH:14][NH2:15]>CCO>[CH3:13][N:14]1[C:10](=[O:12])[CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:1]=[N:15]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 5289058Ortho-formylphenylacetic acid

Product 1

HCID 222436793-methyl-3H-benzo[d][1,2]diazepin-4(5H)-oneYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ortho-formylphenylacetic acid (10 g, 61 mmol) (Bleasdale, et al., J. Chem. Soc. Perkin Trans., 1991, 1683) in 60 mL of EtOH was added N-methylhydrazine (4.2 g, 91 mmol) and refluxed for 1 h. The reaction mixture cooled, solvent removed and transferred the crude reaction mixture to a vacuum sublimation apparatus. The imine was heated at 140° C. under high vacuum for 1 h and collected the cyclized product by extracting with hot 20% ethyl acetate in hexane (Nagarajan, et al., J. Med. Chem., 1972, 15 (10), 1091). The product was crystallized from 20% ethyl acetate in hexane. 4,5-dihydro-3-methyl-3H-2,3-benzodiazepin-4-one was obtained in 50% yield.

Workup

  1. temperaturerefluxed for 1 h
  2. temperatureThe reaction mixture cooled
  3. customsolvent removed
  4. customreaction mixture to a vacuum sublimation apparatus
  5. customcollected the cyclized product
  6. extractionby extracting with hot 20% ethyl acetate in hexane (Nagarajan, et al., J. Med. Chem., 1972, 15 (10), 1091)
  7. customThe product was crystallized from 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-06380e95c2e3401caa98fae5ced3c3be
Source dataset
uspto-grants-2002_08
Patent number
US06432944B1

Reaction notes

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