Propanal → HCID 86758851, compound

HRID 1060864Notes

Reaction equation

HRID 1060864 reaction equation
[CH:1](=O)[CH2:2][CH3:3].Cl.[O:6]([NH2:11])[CH2:7][CH:8]([CH3:10])[CH3:9].C(=O)([O-])[O-].[K+].[K+].C([O-])(=O)C.[Na+].CO/N=[C:26](\[C:29]1[CH:34]=[C:33]([CH3:35])[N:32]=[C:31](OC2C(C)=CC(C)=CC=2C)[C:30]=1[CH3:46])/[CH2:27][CH3:28].CC1N=C(/C(=N\O)/CC)C2COCN([C:57]3[C:62]([CH3:63])=[CH:61][C:60]([CH3:64])=[CH:59][C:58]=3[CH3:65])C=2N=1>C(O)C>[CH2:7]([O:6][N:11]=[C:26]([C:29]1[C:30]2[C:31](=[C:1]([C:57]3[C:58]([CH3:65])=[CH:59][C:60]([CH3:64])=[CH:61][C:62]=3[CH3:63])[CH:2]=[CH:3][CH:46]=2)[N:32]=[C:33]([CH3:35])[CH:34]=1)[CH2:27][CH3:28])[CH:8]([CH3:10])[CH3:9]

Participants

8

Reactant 6

HCID 527PropanalHCID 11430Potassium CarbonateHCID 517045Sodium AcetateHCID 9923394HCID 9923394, compoundHCID 12696238O-(2-Methylpropyl)hydroxylamine--hydrogen chloride (1/1)HCID 135482215HCID 135482215, compound

Product 1

HCID 86758851HCID 86758851, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-[2-methyl-8-2,4,6-trimethyl-phenyl)quinolin4-yl]-propan-1-one (52 mg), iso-butoxylamine hydrochloride (300 mg), potassium carbonate (50 mg) and sodium acetate (40 mg) in ethanol (2 ml) was stirred at room temperature for 48 hr. The mixture was concentrated to dryness, then diluted with water, brine, and extracted with chloroform. The organic layer was separated, dried (Na2SO4) and concentrated to dryness to give a mixture of the title (Z) and (E)-isomer, respectively. The crude mixture was purified by preparative thin layer chromatography with 7% ethyl acetate in hexane as solvent to give a 6:4 mixture of isomers.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additiondiluted with water, brine
  3. extractionextracted with chloroform
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. customto give
  8. customThe crude mixture was purified by preparative thin layer chromatography with 7% ethyl acetate in hexane as solvent
  9. customto give
  10. additiona 6:4 mixture of isomers

Sources & evidence

ORD record
ord-c277eb70691e4f7bba28d8d15c54f6d8
Source dataset
uspto-grants-2003_02
Patent number
US06525067B1

Reaction notes

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