Hydroxyamine hydrochloride → HCID 73508189, compound

HRID 2259308Notes

Reaction equation

HRID 2259308 reaction equation
ClCC([O:5][C:6]1[CH:14]=[CH:13][C:12]2[N:11]([CH3:15])[C:10]3[C:16](=O)[CH2:17][CH2:18][C:9]=3[C:8]=2[CH:7]=1)=O.CC([O-])=O.[Na+].Cl.[NH2:26][OH:27]>CCO.O>[OH:27][N:26]=[C:16]1[C:10]2[N:11]([CH3:15])[C:12]3[CH:13]=[CH:14][C:6]([OH:5])=[CH:7][C:8]=3[C:9]=2[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 19003099HCID 19003099, compound

Product 1

HCID 73508189HCID 73508189, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

7-Chloroacetyloxy-1,4-dihydro-4-methylcyclopent[b]indol-3(2H)-one (8.0 g) was suspended in EtOH (200 ml) and a solution of NaOAc (15.6 g) in water (25 ml) and a solution of hydroxylamine hydrochloride (8.0 g) in water (25 ml) were added and the mixture was refluxed for 3 hours. The mixture was concentrated in vacuo and the residue was recrystallized from 95% EtOH to provide 3-hydroxyimino-4-methyl-1,2,3,4-tetrahydrocyclopent[b]indol-7-ol as an off-white solid. The oxime was dissolved in tetrahydrofuran (100 ml), and thereafter acetic anhydride (8.1 g) and 4-dimethylaminopyridine (400 mg) were added and the mixture was stirred under nitrogen at ambient temperature overnight. The mixture was concentrated in vacuo, CH2Cl2 (100 ml) was added and the solution was washed successively with water (50 ml), 5% NaHCO3 (50 ml) and water (50 ml). After drying (Na2SO4), the solvent was removed in vacuo and the product recrystallized from EtOH to provide 3-acetyloximino-4-methyl-1,2,3,4-tetrahydrocyclopent[b]indol-7-yl acetate (1.7 g).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was recrystallized from 95% EtOH

Sources & evidence

ORD record
ord-242121dd41f84c49a8db523db3085443
Source dataset
uspto-grants-1995_12
Patent number
US05472975

Reaction notes

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