Hydrazine → O-(naphthalen-1-ylmethyl)hydroxylamine

HRID 1271787Notes

Reaction equation

HRID 1271787 reaction equation
[C:1]1([CH2:11][O:12][N:13]2C(=O)C3=CC=CC=C3C2=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.NN>CCO>[C:1]1([CH2:11][O:12][NH2:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22131440N-(1-naphthyl)methoxyphthalimide

Product 1

HCID 15009996O-(naphthalen-1-ylmethyl)hydroxylamineYield 69.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(1-naphthyl)methoxy phthalimide (1.21 g) was suspended in 95% EtOH and hydrazine (0.20 mL) was added. The reaction mixture was stirred overnight 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 (480 mg) as a colorless oil. MS(CI) m/e 174 (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-bbb41a4ded9041cabae7f2f589e8c892
Source dataset
uspto-grants-2007_04
Patent number
USRE039591E1

Reaction notes

Loading…