Hydrazine → Hydrazinecarboxylic acid, phenyl ester
Reaction equation
[NH2:1][NH2:2].Cl[C:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5]>CCOCC>[NH:1]([C:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])[NH2:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of hydrazine (0.83 mL, 26 mmol) in ether was added phenyl chloroformate (0.92 mL, 7.4 mmol) at −20° C. The solution was stirred for 1 h, removed solid by filtration, and filtrate was concentrated to give phenyl hydrazinecarboxylate. To phenyl hydrazinecarboxylate was added compound 2b (1.2 g, 5.2 mmol), THF (20 mL), and DIPEA (1.5 mL) and the solution was stirred for 1 h. Partitioned reaction between sat. aq. NaHCO3 and CH2Cl2, dried (MgSO4), filtered, and concentrated to yield compound 81a (400 mg, 22%).
Workup
- customremoved solid
- filtrationby filtration, and filtrate
- concentrationwas concentrated
Sources & evidence
- ORD record
- ord-46c70f04a18b48ae8e42b25d80a6957d
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415353B2
Reaction notes
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