Methylhydrazine → HCID 19789730, compound

HRID 1655931Notes

Reaction equation

HRID 1655931 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][O:8][N:9]1C(=O)C2=CC=CC=C2C1=O.CNN>ClCCl>[CH3:1][O:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][O:8][NH2:9]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 19789717HCID 19789717, compound

Product 1

HCID 19789730HCID 19789730, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N[3-(methoxymethoxy)propoxy]phthalimide (4.5 g, 17 mmol) in dry dichloromethane (50 ml) was cooled to 0°-5° and treated with N-methylhydrazine (1.2 g, 26 mmol). The reaction mixture was stirred for 2 hr then filtered and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica eluting with hexane:ethyl acetate (60:40) to give the title compound as a colourless oil (1.1 g, 50%). νmax (Film) 3310, 3240, 3160, 2960, 2910, 1590, 1465, and 1380 cm-1 ; δH (CDCl3) 2.07 (2H, quintet, J=6.3 Hz, CH2CH2CH2), 3.38 (3H, s, CH3O), 3.50 (2H, t, J=6.3 Hz, CH2OCH2OCH3), 3.70 (2H, t, J 6.3 Hz, CH2ONH2), 4.66 (2H, s, OCH 2 O), 5.2-5.5 (2H, br.s, D2O exchangeable, NH2).

Workup

  1. filtrationthen filtered
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica eluting with hexane:ethyl acetate (60:40)

Sources & evidence

ORD record
ord-7051549d8ede4290aec95cf184b34a90
Source dataset
uspto-grants-1993_10
Patent number
US05252575

Reaction notes

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