Methyl iodide → Methyl 5-cyano-2-methoxybenzoate

HRID 1397402Notes

Reaction equation

HRID 1397402 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].[C:14]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10583428Methyl 5-cyano-2-hydroxybenzoate

Product 1

HCID 18464789Methyl 5-cyano-2-methoxybenzoateYield 28%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A solution of acid methyl 5-cyano-2-hydroxybenzoate (2 g, 11.2 mmol) in dry acetone (50 mL) was cooled to 0° C. and K2CO3 (2.34 g, 16.9 mmol) followed by MeI (1.1 mL, 16.9 mmol) were added dropwise. The reaction mixture was allowed to stir at 65° C. for 10 h and then diluted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to yield methyl 5-cyano-2-methoxybenzoate (600 mg, crude), which was carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 8.11 (d, J=2.2 Hz, 1H), 7.78-7.74 (dd, J=8.8 Hz, 2.2 Hz, 1H), 7.08-7.05 (d, J=8.8 Hz, 1H), 3.98 (s, 3H), 3.92 (s, 3H). MS (ESI) m/z: Calculated for C10H9NO3: 191.06. found: 191.8 (M+H)+.

Workup

  1. additionwere added dropwise
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a3b89f87a904c3292c19142565c50f8
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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