Water → Methyl 2-methoxy-3-nitrobenzoate

HRID 1961835Notes

Reaction equation

HRID 1961835 reaction equation
[OH:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:15]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH3:15][O:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 596904Methyl 2-hydroxy-3-nitrobenzoate

Product 1

HCID 590805Methyl 2-methoxy-3-nitrobenzoateYield 98.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of methyl 2-hydroxy-3-nitrobenzoate (26.8 g, 136 mmol) in DMF (200 mL) was added K2CO3 (61 g, 440 mmol). Then iodomethane (62 g, 436 mmol) was added dropwise to the mixture at rt. The mixture was stirred at 45° C. for 5 h. Then the mixture was cooled to rt and water was added. The reaction mixture was extracted with EtOAc (500 mL×2). The combined organic layers were washed with water successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound of Step B (28.4 g, 98.8% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.10 (dd, J=1.8 Hz, 8.4 Hz, 1H), 8.00 (dd, J=1.3 Hz, 8.2 Hz, 1H), 7.40 (dd, J=8.2 Hz, 8.4 Hz, 1H), 3.87 (s, 3H), 3.85 (s, 3H).

Workup

  1. temperatureThen the mixture was cooled to rt
  2. extractionThe reaction mixture was extracted with EtOAc (500 mL×2)
  3. washThe combined organic layers were washed with water successively
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f60fecfa795a4a8eb50e57487533b490
Source dataset
uspto-grants-2013_04
Patent number
US08415345B2

Reaction notes

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