Hydroxyamine hydrochloride → 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carbaldehyde oxime

HRID 644069Notes

Reaction equation

HRID 644069 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([CH:19]=O)=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+]>C(O)C.O>[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([CH:19]=[N:22][OH:23])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 860732881-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbaldehyde

Product 1

HCID 860732891-cyclohexylmethyl-7-methoxy-1H-indole-3-carbaldehyde oximeYield 44.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbaldehyde (780 mg, 2.9 mmol) in a mixture of ethanol (8 ml) and water (2 ml) was added hydroxylamine hydrochloride (403 mg, 5.8 mmol) and sodium acetate (713 mg, 8.7 mmol) and the solution stirred for 64 h at room temperature. The mixture was concentrated in vacuo and the residue diluted with water (50 ml) and extracted with ethyl acetate (3×50 ml). The product was recrystallised from diethyl ether/hexane to yield 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carbaldehyde oxime (380 mg, 1.3 mmol) as a yellow powder.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue diluted with water (50 ml)
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. customThe product was recrystallised from diethyl ether/hexane

Sources & evidence

ORD record
ord-9a204dc13a684b9faaa02ef2174d2016
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

Loading…