Hydroxyamine hydrochloride → HCID 136403367, compound

HRID 2259300Notes

Reaction equation

HRID 2259300 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C:7]3[C:12](=O)[CH2:13][CH2:14][C:6]=3[C:5]=2[CH:4]=1.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>CCO.O>[OH:18][N:17]=[C:12]1[C:7]2[NH:8][C:9]3[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[C:6]=2[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 10856521HCID 10856521, compound

Product 1

HCID 136403367HCID 136403367, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A stirred solution of 1,2-cyclopentadione mono-4-methoxyphenylhydrazone (6.0 g) in 100 ml of 10% aqueous H2SO4 was heated on a steam bath for 4 hours and thereafter allowed to cool to room temperature and filtered to give 1,4-dihydro 7-methoxycyclopent[b]indol-3(2H)-one as a solid. To the indole (2.6 g) in 25 ml of 95% EtOH was added hydroxylamine hydrochloride (1.7 g) in 15 ml water followed by sodium acetate (2.1 g) in 15 ml water. The mixture was heated at reflux for 2.5 hours and allowed to stand overnight. The EtOH was removed in vacuo and the solid material which formed was collected and purified by flash chromatography to give 0.8 g of a mixture of oxime isomers.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2.5 hours
  3. customThe EtOH was removed in vacuo
  4. customthe solid material which formed
  5. customwas collected
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-ca788de9486e4917b95a3309efab668b
Source dataset
uspto-grants-1995_12
Patent number
US05472975

Reaction notes

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