Hydroxyamine hydrochloride → HCID 86656076, compound

HRID 1925568Notes

Reaction equation

HRID 1925568 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]2[C:19]3[N:18]4[CH:20]=[CH:21][CH:22]=[C:17]4[C:16](=O)[C:15]=3[CH:14]=[CH:13][CH:12]=2)[CH:2]=1.[ClH:24].[NH2:25][OH:26]>N1C=CC=CC=1>[ClH:24].[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]2[C:19]3[N:18]4[CH:20]=[CH:21][CH:22]=[C:17]4[C:16](=[N:25][OH:26])[C:15]=3[CH:14]=[CH:13][CH:12]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 67072816HCID 67072816, compound

Product 1

HCID 86656076HCID 86656076, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 100 ml round-bottomed flask, a mixture of 231 mg of 5-quinolin-3-ylpyrrolo[1,2-a]indol-9-one obtained according to the preceding stage and 164 mg of hydroxylamine hydrochloride in 20 ml of pyridine is refluxed under argon. After heating for 1.5 hours, the reaction medium is evaporated to dryness under vacuum. The residue is taken up in a saturated solution of sodium bicarbonate and extracted twice with ethyl acetate. The combined organic phases are washed with a saturated solution of sodium bicarbonate and then a saturated solution of sodium chloride, dried over magnesium sulphate, and evaporated to dryness under vacuum. The residue is chromatographed on silica gel (15-40 μm), elution being carried out with a gradient of methanol (2% to 3% v/v) in dichloromethane. 277 mg of 5-quinolin-3-ylpyrrolo[1,2-a]indol-9-one oxime hydrochloride are obtained in the form of a yellowish solid, the characteristics of which are the following:

Workup

  1. customobtained
  2. temperatureis refluxed under argon
  3. temperatureAfter heating for 1.5 hours
  4. customthe reaction medium is evaporated to dryness under vacuum
  5. extractionextracted twice with ethyl acetate
  6. washThe combined organic phases are washed with a saturated solution of sodium bicarbonate
  7. dry with materiala saturated solution of sodium chloride, dried over magnesium sulphate
  8. customevaporated to dryness under vacuum
  9. customThe residue is chromatographed on silica gel (15-40 μm), elution

Sources & evidence

ORD record
ord-6cc00c035d3f4aa2a7c8ed9a99110df2
Source dataset
uspto-grants-2012_05
Patent number
US08178687B2

Reaction notes

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