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

HRID 709533

반응식

HRID 709533 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c06de96ab2594949803c90575a76cad7
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181216B2

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