Hydrazine → Hydrazinecarboxylic acid, phenyl ester

HRID 1961617Notes

Reaction equation

HRID 1961617 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

HCID 9321HydrazineHCID 15891Phenyl chloroformate

Product 1

HCID 134791Hydrazinecarboxylic acid, phenyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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

  1. customremoved solid
  2. filtrationby filtration, and filtrate
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-46c70f04a18b48ae8e42b25d80a6957d
Source dataset
uspto-grants-2013_04
Patent number
US08415353B2

Reaction notes

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