Hydrazine → 2-(4-Bromophenoxy)acetohydrazide
Reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](O)=[O:9])=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:25][NH2:26]>C1COCC1>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([NH:25][NH2:26])=[O:9])=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (4-bromophenoxy)acetic acid (1.0 g, 4.3 mmol) in THF (15 mL) was added N,N-Carbonyldiimidazole (0.84 g, 5.2 mmol). After refluxing for 2 hours, hydrazine (0.6 g, 20 mmol) was added to the reaction mixture slowly with a syringe at 0° C. The reaction mixture was allowed to warm to room temperature slowly and then concentrated to yield the desired product as a white solid. LCMS calculated for C8H10BrN2O2 (M+H): 245.0. found: 244.9, 246.9.
Workup
- temperatureAfter refluxing for 2 hours
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f0ff9de76d784a37b53ff13824502983
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863285B2
Reaction notes
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