Hydrazine hydrate (1:1) → HCID 21244208, compound

HRID 621143Notes

Reaction equation

HRID 621143 reaction equation
[CH3:1][C:2]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:17])([O:4][N:5]1C(=O)C2=CC=CC=C2C1=O)[CH3:3].O.NN>C(Cl)Cl>[CH3:3][C:2]([O:4][NH2:5])([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:17])[CH3:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 14230770HCID 14230770, compound

Product 1

HCID 21244208HCID 21244208, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 80 ml of methylene chloride is dissolved 7.68 g of N-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxy]phthalimide and under ice-cooling and stirring 0.97 ml of hydrazine hydrate is added. The mixture is stirred at room temperature for 2 hours, after which 0.97 ml of hydrazine hydrate is further added. The mixture is stirred for 3 hours and the resultant crystalline precipitate is separated by filtration and washed with methylene chloride. The filtrate and washings are combined and further washed with diluted aqueous ammonia and water in this order, and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is chromatographed on a silica gel column [silica gel: 300 g; eluent: ethyl acetate-hexane (1:1)] to give 4.58 g of O-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyl]hydroxylamine as a yellow oil. This product solidifies on cooling.

Workup

  1. temperatureunder ice-cooling
  2. additionis added
  3. stirringThe mixture is stirred for 3 hours
  4. customthe resultant crystalline precipitate is separated by filtration
  5. washwashed with methylene chloride
  6. washfurther washed with diluted aqueous ammonia and water in this order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent is then distilled off under reduced pressure
  9. customthe residue is chromatographed on a silica gel column [silica gel: 300 g; eluent: ethyl acetate-hexane (1:1)]

Sources & evidence

ORD record
ord-60e58a459a294394b9099140c20eeb93
Source dataset
uspto-grants-1989_04
Patent number
US04822788

Reaction notes

Loading…