Benzamide → 2-Methylbenzamide

HRID 2294986Notes

Reaction equation

HRID 2294986 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:12]1COCC1>>[CH3:12][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:1]([NH2:9])=[O:8]

Participants

4

Reactant 3

HCID 2331BenzamideHCID 8028TetrahydrofuranHCID 24758Sodium hydride

Product 1

HCID 107042-MethylbenzamideYield 91%

Conditions

Temperature
60 °C

Procedure

Treat the product of step 5 (10.54 g, 23.3 mmol) in THF (170 mL) with 60% NaH (1.87 g, 47 mmol) followed by CH31I (1.9 mL, 30.5 mmol). Heat the reaction mixture at 60° C. for 30 min and then partition between Et2O (250 mL) and H2O (500 mL). Extract the aqueous layer with Et2O (500 mL), wash the combined organic layers with brine (250 mL), dry with MgSO4 and concentrate to give 9.9 g of the methyl benzamide product as a colorless oil (21 mmol, 91%).

Workup

  1. custompartition between Et2O (250 mL) and H2O (500 mL)
  2. extractionExtract the aqueous layer with Et2O (500 mL)
  3. washwash the combined organic layers with brine (250 mL)
  4. dry with materialdry with MgSO4
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-abf4c5585b66423eb4482d2e0f9fdf6c
Source dataset
uspto-grants-1997_11
Patent number
US05691362

Reaction notes

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