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

HRID 71141Notes

Reaction equation

HRID 71141 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-869dd976f4ec4aa9be54cc39e0b1660f
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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