Hydroxyamine hydrochloride → 5-(6-fluoro-1H-benzimidazol-2-yl)pyrrolo[1,2-a]indol-9-one oxime

HRID 1925565Notes

Reaction equation

HRID 1925565 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]3[C:18]4[N:17]5[CH:19]=[CH:20][CH:21]=[C:16]5[C:15](=O)[C:14]=4[CH:13]=[CH:12][CH:11]=3)[NH:7][C:6]=2[CH:23]=1.Cl.[NH2:25][OH:26]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]3[C:18]4[N:17]5[CH:19]=[CH:20][CH:21]=[C:16]5[C:15](=[N:25][OH:26])[C:14]=4[CH:13]=[CH:12][CH:11]=3)[NH:7][C:6]=2[CH:23]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 670729195-(6-fluoro-1H-benzimidazol-2-yl)pyrrolo[1,2-a]indol-9-one

Product 1

HCID 866560755-(6-fluoro-1H-benzimidazol-2-yl)pyrrolo[1,2-a]indol-9-one oximeYield 154%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 20 ml round-bottomed flask, a mixture of 60 mg of 5-(6-fluoro-1H-benzimidazol-2-yl)pyrrolo[1,2-a]indol-9-one obtained according to the preceding stage and 42 mg of hydroxylamine hydrochloride in 5 ml of pyridine is brought to reflux for 6 hours. The reaction medium is evaporated to dryness under vacuum and the residue taken up with 25 ml of a saturated solution of sodium bicarbonate is extracted with 3 times 25 ml of ethyl acetate. The combined organic phases are washed with 25 ml of a saturated solution of sodium chloride, dried over magnesium sulphate, and evaporated to dryness under vacuum. 97 mg of 5-(6-fluoro-1H-benzimidazol-2-yl)pyrrolo[1,2-a]indol-9-one oxime are obtained in the form of a yellowish oil, the characteristics of which are the following:

Workup

  1. customobtained
  2. temperatureto reflux for 6 hours
  3. customThe reaction medium is evaporated to dryness under vacuum
  4. extractionis extracted with 3 times 25 ml of ethyl acetate
  5. washThe combined organic phases are washed with 25 ml of a saturated solution of sodium chloride
  6. dry with materialdried over magnesium sulphate
  7. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-307c0d8e57b94698b0c572d55bd0664a
Source dataset
uspto-grants-2012_05
Patent number
US08178687B2

Reaction notes

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