Hydrazine hydrate (1:1) → 3-Methoxy-4-(2-methyloxazol-5-yl)benzohydrazide
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]1[O: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[C:12]1[O:16][C:15]([CH3:17])=[N:14][CH:13]=1)[C:6]([NH:19][NH2:20])=[O:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
N,N′-Carbonyldiimidazole (115 g) was added to a suspension of 3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzoic acid (83.0 g) in THF (1 L) at room temperature, and the mixture was stirred for 1 hr. The reaction mixture was cooled to −10° C., hydrazine monohydrate (173 mL) was added, and the mixture was stirred at room temperature for 16 hr. The solvent in the reaction mixture was evaporated under reduced pressure, and water was added to the residue. The resultant solid was collected by filtration, washed with water, dried under reduced pressure, and washed with IPE to give the title compound (85.8 g).
Workup
- stirringthe mixture was stirred at room temperature for 16 hr
- customThe solvent in the reaction mixture was evaporated under reduced pressure, and water
- additionwas added to the residue
- filtrationThe resultant solid was collected by filtration
- washwashed with water
- customdried under reduced pressure
- washwashed with IPE
Sources & evidence
- ORD record
- ord-5a0c6204eb8d498e8a613db833cb2c94
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822699B2
Reaction notes
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