Hydroxyamine hydrochloride → HCID 13489807, compound

HRID 364844Notes

Reaction equation

HRID 364844 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])[CH:5]=[O:6].Cl.NO>C(O)C>[N+:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[CH:3]=[N:2][O:6][CH:5]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 3557290HCID 3557290, compound

Product 1

HCID 13489807HCID 13489807, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 75 g of 3-(dimethylamino)-2-(2-nitrophenyl)acrolein [prepared by the procedure of U. Hengartner et al., J. Org. Chem., 44, 3748 (1979)] and 47.3 g of hydroxylamine hydrochloride in 300 ml of ethanol was refluxed for 10 hours, then concentrated to dryness in vacuo. Water (400 ml) was added to the residue and the suspension filtered. The isolated solid was recrystallized from 2-propanol to yield 56 g of the title compound; m.p. 51°-54° C.

Workup

  1. customprepared by the procedure of U
  2. concentrationconcentrated to dryness in vacuo
  3. additionWater (400 ml) was added to the residue
  4. filtrationthe suspension filtered
  5. customThe isolated solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-b54da3056421435ba09ac031e4712abc
Source dataset
uspto-grants-1986_08
Patent number
US04606755

Reaction notes

Loading…