Acetohydrazide → HCID 67036847, compound

HRID 1920058Notes

Reaction equation

HRID 1920058 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.[C:17]([NH:20][NH2:21])(=[O:19])[CH3:18]>O1CCCC1>[C:17]([NH:20][NH:21][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 219286243,4-Dimethoxy-5-nitrobenzoic acid

Product 1

HCID 67036847HCID 67036847, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3,4-dimethoxy-5-nitrobenzoic acid (0.438 g, 1.93 mmol) in tetrahydrofuran (10 mL) at room temperature was added 1,1-carbonyldiimidazole (0.343 g, 2.12 mmol) in one portion and the mixture was stirred at room temperature for one hour, then at 70° C. for two hours, whereupon acetic hydrazide (0.157 g, 2.12 mmol) was added. The resulting was stirred at room temperature for thirty minutes, then at 70° C. for two hours. After cooling to room temperature, the mixture was poured onto ice-water (100 mL) and the precipitate was filtered off and washed with water. 3,4-Dimethoxy-5-nitro-benzoic acid N′-acetyl-hydrazide was obtained as a white solid (0.296 g, 54%).

Workup

  1. waitat 70° C. for two hours
  2. stirringThe resulting was stirred at room temperature for thirty minutes
  3. waitat 70° C. for two hours
  4. temperatureAfter cooling to room temperature
  5. additionthe mixture was poured onto ice-water (100 mL)
  6. filtrationthe precipitate was filtered off
  7. washwashed with water

Sources & evidence

ORD record
ord-38b80567b6e14758bc66ec6d32a41c32
Source dataset
uspto-grants-2012_05
Patent number
US08168793B2

Reaction notes

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