Methane → N-cyclopropyl-5-(3-methoxypropyl)-2,3-dimethylbenzamide

HRID 337617Notes

Reaction equation

HRID 337617 reaction equation
[CH:1]1([NH:4][C:5](=[O:19])[C:6]2[CH:11]=[C:10](/[CH:12]=[CH:13]/[CH2:14][O:15][CH3:16])[CH:9]=[C:8]([CH3:17])[C:7]=2[CH3:18])[CH2:3][CH2:2]1.C>CCOC(C)=O.[Pd]>[CH:1]1([NH:4][C:5](=[O:19])[C:6]2[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:9]=[C:8]([CH3:17])[C:7]=2[CH3:18])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 297MethaneHCID 67062080N-Cyclopropyl-5-[(1E)-3-methoxy-1-propen-1-yl]-2,3-dimethylbenzamide

Product 1

HCID 67061921N-cyclopropyl-5-(3-methoxypropyl)-2,3-dimethylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-Cyclopropyl-5-[(1E)-3-methoxy-1-propen-1-yl]-2,3-dimethylbenzamide (1 eq.) from the previous step and 10% w/w palladium over charcoal (0.05 eq.) were suspended in EtOAc (0.2 M). The vessel was then evacuated and purged with H2. Under a balloon-filled H2 atmosphere, the reaction suspension was stirred at RT for 6 h. The reaction suspension was then filtered through a bed of celite and the filtrate concentrated in vacuo to afford the title compound as a white solid.

Workup

  1. customThe vessel was then evacuated
  2. custompurged with H2
  3. filtrationThe reaction suspension was then filtered through a bed of celite
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-8481bc07cd94426ab9007c3641f653f1
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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