Hydroxyamine hydrochloride → HCID 13489807, compound

HRID 2309346Notes

Reaction equation

HRID 2309346 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-3e118736bad1483ca489e183d660bdd5
Source dataset
uspto-grants-1987_09
Patent number
US04695311

Reaction notes

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