Hydroxyamine hydrochloride → HCID 20368783, compound

HRID 616719Notes

Reaction equation

HRID 616719 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[C:7](=O)[CH2:8][N+:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.Cl.[NH2:24]O>O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:7]2[N:24]=[C:10]3[CH:11]=[CH:12][C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:9]3[CH:8]=2)[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 10642113HCID 10642113, compound

Product 1

HCID 20368783HCID 20368783, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a steel bomb having an internal glass coating, 9.34 g. of 1-(3-methoxyphenacyl)quinolinium bromide is heated at 130° C. for 24 hours together with 2.17 g. of hydroxylamine hydrochloride dissolved in 39 ml. of water. After cooling, the resulting solid precipitate is boiled with 60 ml. of water and recovered by filtration. The solid product is suspended in 50 ml. of water and concentrated ammonium hydroxide is added to the suspension. The mixture is extracted with dichloromethane and the organic extract is evaporated to dryness. By crystallization from methanol, 4.5 g. of the title product is obtained which melts at 129°-31° C.

Workup

  1. temperatureAfter cooling
  2. filtrationof water and recovered by filtration
  3. additionof water and concentrated ammonium hydroxide is added to the suspension
  4. extractionThe mixture is extracted with dichloromethane
  5. extractionthe organic extract
  6. customis evaporated to dryness
  7. customBy crystallization from methanol, 4.5 g

Sources & evidence

ORD record
ord-83a083bc24b04dcab0f9b64c344976be
Source dataset
uspto-grants-1978_02
Patent number
US04075342

Reaction notes

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