Hydrazine hydrate (1:1) → 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzohydrazide

HRID 1398170Notes

Reaction equation

HRID 1398170 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1)[C:6](O)=[O:7].O.[NH2:19][NH2:20]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1)[C:6]([NH:19][NH2:20])=[O:7]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 579317633-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzoic acid

Product 1

HCID 666078503-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzohydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzoic acid (5 g) in THF (60 mL) was added N,N′-carbonyldiimidazole (6.98 g) at room temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was cooled to −10° C., hydrazine monohydrate (10.44 mL) was added, and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, and water was added. The precipitated solid was collected by filtration to give the title compound (0.70 g).

Workup

  1. temperatureThe reaction mixture was cooled to −10° C.
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. customThe solvent was evaporated under reduced pressure, and water
  4. additionwas added
  5. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-c585eec9b5984d038ad238f2b6f445f0
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

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