Methyl iodide → 2-amino-6-methoxy-N-methylbenzamide

HRID 1834309Notes

Reaction equation

HRID 1834309 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([O:11][CH3:12])[C:7]=1[C:8]([NH2:10])=[O:9].[H-].[Na+].[CH3:15]I>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([O:11][CH3:12])[C:7]=1[C:8]([NH:10][CH3:15])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 122648142-Amino-6-methoxybenzamide

Product 1

HCID 122648202-amino-6-methoxy-N-methylbenzamideYield 8.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
3 °C

Procedure

Slow addition of 4.98 g. (0.03 mole) of 6-amino-o-anisamide to a mixture of 57% NaH (1.32 g., 0.0315 mole) in 50 ml. dimethylformamide was carried out at room temperature. After the evolution of H2 ceased, the mixture was cooled to 3° C. and 2.06 ml. (0.033 mole) of methyliodide was slowly added at 3°-5° C. The temperature was allowed to go up to room temperature and stir for 2 hours. The mixture was concentrated, the residue extracted into ethyl acetate-water, the mixture was basified, and the ethyl acetate layer was washed with water, brine and dried. Concentration gave a tan solid that was crystallized (ethanol), giving 0.45 g (8%) Of 6-amino-N-methyl-o-anisamide m.p. 186°-189° C.

Workup

  1. additionSlow addition of 4.98 g
  2. customwas carried out at room temperature
  3. customto go up to room temperature
  4. concentrationThe mixture was concentrated
  5. extractionthe residue extracted into ethyl acetate-water
  6. washthe ethyl acetate layer was washed with water, brine
  7. customdried
  8. concentrationConcentration
  9. customgave a tan solid
  10. customthat was crystallized (ethanol)

Sources & evidence

ORD record
ord-0d8e7e3904d94badb87db7f4cdf6afe8
Source dataset
uspto-grants-1978_01
Patent number
US04069343

Reaction notes

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