Methyl iodide → Benzoic acid, 2-methoxy-5-nitro-, methyl ester

HRID 59241Notes

Reaction equation

HRID 59241 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[C:15]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([O:7][CH3:15])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2841632-Methoxy-5-nitrobenzoic acid

Product 1

HCID 7020925Benzoic acid, 2-methoxy-5-nitro-, methyl esterYield 78.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-methoxy-5-nitrobenzoic acid (25.0 g, 0.12 mol) in DMF (100 mL) was added K2CO3 (26.3 g, 0.19 mol). The reaction mass was stirred at 80° C. for 1 h followed by addition of methyl iodide (12.3 mL, 0.19 mol). The reaction mass was further stirred at 80° C. for 5-6 h. The reaction mass was filtered and the obtained filtrate was concentrated. The residue was further diluted with water and obtained solid was filtered off to afford 20.0 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.83 (s, 3H), 3.97 (s, 3H), 7.38 (d, 0.1=9.3 Hz, 1H), 8.41 (dd, J=2.4 Hz & 2.4 Hz, 1H), 8.47 (s, 1H); MS (m/z): 212.44 (M+H)+.

Workup

  1. stirringThe reaction mass was further stirred at 80° C. for 5-6 h
  2. filtrationThe reaction mass was filtered
  3. concentrationthe obtained filtrate was concentrated
  4. additionThe residue was further diluted with water
  5. customobtained solid
  6. filtrationwas filtered off

Sources & evidence

ORD record
ord-38513e2fbf8e4c29ae3fdd9d2ae8ed7f
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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