Sodium Methoxide → 5-{(E)-3-[4-(2-Dimethylamino-ethoxy)-phenyl]-3-oxo-propenyl}-indan-1-one O-methyl oxime

HRID 1593418Notes

Reaction equation

HRID 1593418 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([CH:13]=O)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.C[O-].[Na+].Cl.[CH3:19][N:20]([CH3:33])[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[CH:26][CH:25]=1>CO.O>[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9](/[CH:13]=[CH:31]/[C:30]([C:27]3[CH:28]=[CH:29][C:24]([O:23][CH2:22][CH2:21][N:20]([CH3:19])[CH3:33])=[CH:25][CH:26]=3)=[O:32])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 122143931-[4-(2-Dimethylaminoethoxy) phenyl]ethanone hydrochlorideHCID 730123441H-Indene-5-carboxaldehyde, 2,3-dihydro-1-(methoxyimino)-

Product 1

HCID 865954105-{(E)-3-[4-(2-Dimethylamino-ethoxy)-phenyl]-3-oxo-propenyl}-indan-1-one O-methyl oximeYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of the product of Example 1 Step 2 (1.06 g, 5.6 mmol), sodium methoxide (0.750 g, 13.9 mmol) and 1-[4-(2-dimethylaminoethoxy) phenyl]ethanone hydrochloride (1.36 g, 5.6 mmol) (J. H. Short et al., J. Med. Chem. 1965, 8, 223) in methanol (30 ml) and water (1 ml) was heated under reflux for 5 hours. After cooling to room temperature the solid was collected, washed with cold methanol and diethyl ether and dried to give the title compound (1.74 g, 83%); MS(ES+) m/e 378 [M+H]+.

Workup

  1. temperatureunder reflux for 5 hours
  2. customwas collected
  3. washwashed with cold methanol and diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-887006bc5cfb46bda350c6df0b00d21a
Source dataset
uspto-grants-2007_11
Patent number
US07297694B2

Reaction notes

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