Ethanol → 4-Methoxy-N-{6-[2-(pyridin-2-yl)ethyl]-2H-1,3-benzodioxol-5-yl}benzamide

HRID 1659276Notes

Reaction equation

HRID 1659276 reaction equation
[CH2:1]1[O:17][C:16]2[C:3](=[CH:4][C:5]([N+:18]([O-])=O)=[C:6]([CH:15]=2)[CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[O:2]1.C(O)C.[C:24](Cl)(=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1>[Pd].C(OCC)(=O)C>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]([NH:18][C:5]2[CH:4]=[C:3]3[O:2][CH2:1][O:17][C:16]3=[CH:15][C:6]=2[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:33])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 7477p-Anisoyl chlorideHCID 356499Pyridine, 2-[2-(6-nitro-1,3-benzodioxol-5-yl)ethenyl]-

Product 1

HCID 205599614-Methoxy-N-{6-[2-(pyridin-2-yl)ethyl]-2H-1,3-benzodioxol-5-yl}benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(4,5-Methylenedioxy-2-nitrostyryl)pyridine (10.8 g., 0.04 mole) is hydrogenated on a Parr apparatus in 200 ml. of ethanol with 2.0 g. of 10% palladium on carbon as catalyst. After the reduction is complete, the mixture is filtered and the solvent evaporated. The residue consisting of 2-(4,5-methylenedioxy-2-aminophenethyl)pyridine is immediately dissolved in pyridine (100 ml.) and anisoyl chloride (7.5 g., 0.044 mole) added. The solution is stirred for 30 min. A basic workup according to the procedure of Example 25 affords 10 g. of 4-methoxy-4',5'-methylenedioxy-2'-[2-(2-pyridyl)ethyl]benzanilide obtained analytically pure by crystallization from ethyl acetate.

Workup

  1. filtrationthe mixture is filtered
  2. customthe solvent evaporated
  3. dissolutionis immediately dissolved in pyridine (100 ml.)
  4. customaffords 10 g

Sources & evidence

ORD record
ord-f817c42a6ded4aec9c7e8a7aeba6a9c8
Source dataset
uspto-grants-1981_12
Patent number
USRE030812

Reaction notes

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