Methyl iodide → HCID 21966470, compound

HRID 2212611Notes

Reaction equation

HRID 2212611 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[CH3:8].[C:15](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:15][O:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:14])[CH:11]([CH3:12])[CH3:13])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 837248HCID 837248, compound

Product 1

HCID 21966470HCID 21966470, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(3-hydroxy-4-methyl-phenyl)-isobutyramide (6.48 g, 33.5 mmol) was dissolved in 40 mL of acetone, potassium carbonate (13.9 g, 100.5 mmol) was added followed by methyl iodide (14.3 g, 100.5 mmol). The mixture was stirred at room temperature for about 3 days. The solution was filtered and evaporated under reduced pressure to give 6.6 g of N-(3-methoxy-4-methyl-phenyl)-isobutyramide (95%). 1H NMR (300 MHz, CDCl3, ppm): δ: 1.26 (d, J=7.03 Hz, 6 H), 2.17 (s, 3 H), 2.49 (m, 1 H), 3.83 (s, 3 H), 6.71 (dd, J=2.05 Hz, 8.21 Hz, 1 H), 7.02 (d, J=7.91 Hz, 1 H), 7.11 (bs, 1 H), 7.47 (d, J=1.76 Hz, 1 H).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7d17bf8c0e3f4b93bd7a297ff07f6866
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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