Hydrazine → O-(quinolin-4-ylmethyl)hydroxylamine

HRID 1271779Notes

Reaction equation

HRID 1271779 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][O:12][N:13]2C(=O)C3=CC=CC=C3C2=O)=[CH:3][CH:2]=1.NN>CCO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][O:12][NH2:13])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22131435N-(4-quinolyl)methoxyphthalimide

Product 1

HCID 22131436O-(quinolin-4-ylmethyl)hydroxylamineYield 125.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-quinolyl)methoxy phthalimide (2.00 g) was suspended in 95% EtOH and hydrazine (0.30 mL) was added. The reaction mixture was stirred for 3 h and then filtered. The filtrate was concentrated under reduced pressure and then taken up in a small amount of dichloromethane. The small amount of remaining phthalhydrazide was then removed by filtration. The filtrate was concentrated under reduced pressure to give the title compound (1.44 g) as a yellow oil. MS(CI) m/e 175 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe small amount of remaining phthalhydrazide was then removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c2644a113b9d4933928853a7b287b3a3
Source dataset
uspto-grants-2007_04
Patent number
USRE039591E1

Reaction notes

Loading…