Hydroxyamine hydrochloride → 3,4-Dihydro-4-methylcyclopent[b]indol-1(2H)-one oxime

HRID 2379135Notes

Reaction equation

HRID 2379135 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[C:11](=O)[CH2:12][CH2:13][C:3]1=2.Cl.[NH2:16][OH:17]>N1C=CC=CC=1>[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[C:11](=[N:16][OH:17])[CH2:12][CH2:13][C:3]1=2

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 118162844-methyl-2,3-dihydrocyclopenta[b]indol-1(4H)-one

Product 1

HCID 6033473,4-Dihydro-4-methylcyclopent[b]indol-1(2H)-one oximeYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,4-Dihydro-4-methylcyclopent[b]indol-1(2H)-one (1.7 g) and hydroxylamine hydrochloride (1.925 g) in pyridine were heated at 60° for 18 h and cooled. The reaction mixture was evaporated in vacuo to a residue to which was added 8% sodium bicarbonate (150 ml). Extraction with ethyl acetate (300 ml) produced a suspension in the organic layer; this layer and associated solid was separated from the aqueous layer. The aqueous layer was re-extracted with ethyl acetate (250 ml). The combined organic extracts (and suspended solid) were evaporated to a residue, boiled with a mixture of ethanol (150 ml) and methanol (150 ml) and cooled to ca. 50°. The residue was adsorbed from this solution on to FCC silica and applied to an FCC column. Elution with ethyl acetate/3-10% methanol provided the title compound (1.69 g), m.p. 219°-224° (decomp.).

Workup

  1. temperaturecooled
  2. customThe reaction mixture was evaporated in vacuo to a residue to which
  3. additionwas added 8% sodium bicarbonate (150 ml)
  4. extractionExtraction with ethyl acetate (300 ml)
  5. customproduced a suspension in the organic layer
  6. customthis layer and associated solid was separated from the aqueous layer
  7. extractionThe aqueous layer was re-extracted with ethyl acetate (250 ml)
  8. customThe combined organic extracts (and suspended solid) were evaporated to a residue
  9. additionboiled with a mixture of ethanol (150 ml) and methanol (150 ml)
  10. temperaturecooled to ca. 50°
  11. washElution with ethyl acetate/3-10% methanol

Sources & evidence

ORD record
ord-ce8f1e613f034a89a10091274012692f
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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