Hydrazine → 5-Methyl-7-nitro-2-[1,3,4]oxadiazol-2-yl-1H-indole

HRID 336479Notes

Reaction equation

HRID 336479 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[N+:15]([O-:17])=[O:16])=O.[NH2:18][NH2:19]>CO>[CH3:14][C:10]1[CH:11]=[C:12]2[C:7](=[C:8]([N+:15]([O-:17])=[O:16])[CH:9]=1)[NH:6][C:5]([C:3]1[O:2][CH:1]=[N:18][N:19]=1)=[CH:13]2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 594480925-Methyl-7-nitro-1H-indole-2-carboxylic acid methyl ester

Product 1

HCID 1363372035-Methyl-7-nitro-2-[1,3,4]oxadiazol-2-yl-1H-indoleYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Methyl-7-nitro-1H-indole-2-carboxylic acid methyl ester (234 mg, 1 mmol) prepared in Preparation 15 was dissolved in methanol (10 mL), to which was added hydrazine (3 mL). The reaction solution was refluxed for 3 h, and concentrated under reduced pressure. To the concentrate was added trimethylorthoformate (10 mL), and the mixture was refluxed for 8 h. The reaction mixture was distilled under reduced pressure, and the resulting solid was washed with ethyl acetate to give the title compound (49 mg, Yield 20%).

Workup

  1. temperatureThe reaction solution was refluxed for 3 h
  2. concentrationconcentrated under reduced pressure
  3. additionTo the concentrate was added trimethylorthoformate (10 mL)
  4. temperaturethe mixture was refluxed for 8 h
  5. distillationThe reaction mixture was distilled under reduced pressure
  6. washthe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-144e6811287347799f236c05106e9229
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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