Methylhydrazine → HCID 19917896, compound

HRID 1755875Notes

Reaction equation

HRID 1755875 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][N:13]2C(=O)C3=CC=CC=C3C2=O)=[CH:7][CH:6]=1)=[O:4].CNN>CN(C)C=O>[NH2:13][O:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([C:3]([NH:2][OH:1])=[O:4])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 19917987HCID 19917987, compound

Product 1

HCID 19917896HCID 19917896, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

N-Hydroxy-α-(phthalimidooxy)-p-toluamide (10.0 g) (32 mmol) are suspended in 80 ml of absolute dimethylformamide and treated at -5° C. with 1.86 g (40 mmol) of methylhydrazine. After stirring at room temperature for 2.5 hours 40 ml of solvent are distilled off in a high vacuum at room temperature. Insoluble material is filtered off and washed with a small amount of dimethylformamide. The mother liquor and wash solution are treated with 70 ml of ethanol. After stirring at 0° C. for 1/2 hour the precipitated crystalline product is filtered off under suction and washed with a small amount of ethanol. After drying in a high vacuum at room temperature there are obtained 3.9 g of α-(aminooxy)-N-hydroxy-p-toluamide as white crystals of m.p. 145° C. (dec.).

Workup

  1. distillationare distilled off in a high vacuum at room temperature
  2. filtrationInsoluble material is filtered off
  3. washwashed with a small amount of dimethylformamide
  4. washThe mother liquor and wash solution
  5. additionare treated with 70 ml of ethanol
  6. filtrationis filtered off under suction
  7. washwashed with a small amount of ethanol
  8. customAfter drying in a high vacuum at room temperature

Sources & evidence

ORD record
ord-b80996b928ea4478a4fb2720268fc8f8
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

Loading…