Hydroxyamine hydrochloride → HCID 73677881, compound

HRID 1779488Notes

Reaction equation

HRID 1779488 reaction equation
Cl.[NH2:2][OH:3].[Cl:4][C:5]1[CH:13]=[CH:12][C:11]2[N:10]3[CH:14]=[CH:15][CH:16]=[C:9]3[C:8](=O)[C:7]=2[CH:6]=1>N1C=CC=CC=1>[Cl:4][C:5]1[CH:13]=[CH:12][C:11]2[N:10]3[CH:14]=[CH:15][CH:16]=[C:9]3[C:8](=[N:2][OH:3])[C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 19956218HCID 19956218, compound

Product 1

HCID 73677881HCID 73677881, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Add 3.9 g (56.1 mmol) of hydroxylamine hydrochloride to a solution of 4.6 g (22.6 mmol) of 7-chloropyrrolo[1,2-a]indol-9-one in 80 ml of pyridine, then heat the reaction mixture at reflux for 3 hours. After cooling, the pyridine is removed under reduced pressure and the residue is taken up in water and extracted with 300 ml of diethyl ether. The ethereal phase is washed with 100 ml of 0.5N hydrochloric acid and then with water, dried over magnesium sulfate, rendered colourless with animal charcoal and then concentrated under reduced pressure to yield 4.18 g of the title product.

Workup

  1. temperatureheat the reaction mixture
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. customthe pyridine is removed under reduced pressure
  5. extractionextracted with 300 ml of diethyl ether
  6. washThe ethereal phase is washed with 100 ml of 0.5N hydrochloric acid
  7. dry with materialwith water, dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d18c724ad6c84d26b503a9dfa45c4ac3
Source dataset
uspto-grants-1997_05
Patent number
US05627203

Reaction notes

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