Dimethylformamide → 1,2-Benzenedicarboxylic acid, 3-nitro-, 1,2-dimethyl ester

HRID 1915127Notes

Reaction equation

HRID 1915127 reaction equation
[CH3:1]I.[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:8](C(O)=O)[C:7]=1[C:15]([OH:17])=[O:16])([O-:5])=[O:4].[C:18](=[O:21])(O)[O-].[Na+].CN([CH:26]=[O:27])C>>[CH3:18][O:21][C:26](=[O:27])[C:8]1[C:7](=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=[CH:13][CH:12]=1)[C:15]([O:17][CH3:1])=[O:16]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 690433-Nitrophthalic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 2499121,2-Benzenedicarboxylic acid, 3-nitro-, 1,2-dimethyl esterYield 95%

Procedure

Methyl iodide (30.2 g, 213 mmol) was added to a stirred mixture of 3-nitrophthalic acid (15.0 g, 71.0 mmol) and sodium bicarbonate (23.9 g, 284 mmol) in DMF (150 mL) at room temperature, and the mixture was then heated in an oil bath set to 60° C. for 4 h. The mixture was then poured into 700 mL of ice water. After the ice melted, the mixture was extracted with ethyl acetate (3×150 mL) and the organic phases were washed with water (7×500 mL), dried (MgSO4) and evaporated, providing 16.2 g of 3-nitrophthalic acid dimethyl ester as a pale yellow solid, in 95% yield; 1H NMR (CDCl3) δ 3.95 (s, 3H), 4.02 (s, 3H), 7.69 (t, J=8.1 Hz, 1H), 8.36 (m, 2H).

Workup

  1. temperaturethe mixture was then heated in an oil bath
  2. extractionthe mixture was extracted with ethyl acetate (3×150 mL)
  3. washthe organic phases were washed with water (7×500 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-9eb8363d65c8419780ff0a9f4c944ce1
Source dataset
uspto-grants-2013_12
Patent number
US08614328B2

Reaction notes

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