Hydroxyamine hydrochloride → 5-(3H-imidazo[4,5-c]pyridin-2-yl)pyrrolo[1,2-a]indol-9-one oxime
Reaction equation
[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[NH:3][C:2]=1[C:10]1[C:18]2[N:17]3[CH:19]=[CH:20][CH:21]=[C:16]3[C:15](=O)[C:14]=2[CH:13]=[CH:12][CH:11]=1.Cl.[NH2:24][OH:25]>N1C=CC=CC=1>[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[NH:3][C:2]=1[C:10]1[C:18]2[N:17]3[CH:19]=[CH:20][CH:21]=[C:16]3[C:15](=[N:24][OH:25])[C:14]=2[CH:13]=[CH:12][CH:11]=1Participants
Procedure
In a 250 ml round-bottomed flask under argon, a mixture of 444 mg of 5-(3H-imidazo[4,5-c]pyridin-2-yl)pyrrolo[1,2-a]indol-9-one obtained according to the preceding stage and 323 mg of hydroxylamine hydrochloride in 60 ml of pyridine is refluxed for 3 hours. The reaction medium is evaporated to dryness under vacuum, the residue is taken up in a saturated solution of sodium bicarbonate and the precipitate is filtered off and washed with water. The solid is dissolved in methanol and the solvent is evaporated to dryness under vacuum. The residue is taken up in toluene and then re-evaporated to dryness under vacuum. 380 mg of 5-(3H-imidazo[4,5-c]pyridin-2-yl)pyrrolo[1,2-a]indol-9-one oxime are obtained in the form of a solid, the characteristics of which are the following:
Workup
- customobtained
- temperatureis refluxed for 3 hours
- customThe reaction medium is evaporated to dryness under vacuum
- filtrationthe precipitate is filtered off
- washwashed with water
- dissolutionThe solid is dissolved in methanol
- customthe solvent is evaporated to dryness under vacuum
- customre-evaporated to dryness under vacuum
Sources & evidence
- ORD record
- ord-d0e32a5804494c2d9985f8ba52f230c3
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178687B2
Reaction notes
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