4-Nitrophenol → 4-(4-Nitrophenoxy)furo[2,3-b]pyridine-2-carboxylic acid methyl ester

HRID 1010357Notes

Reaction equation

HRID 1010357 reaction equation
CN1CCCC1=O.C(N(C(C)C)CC)(C)C.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([O-:19])=[O:18].[CH3:27][O:28][C:29]([C:31]1[O:40][C:34]2=[N:35][CH:36]=[CH:37][C:38](Cl)=[C:33]2[CH:32]=1)=[O:30]>O>[CH3:27][O:28][C:29]([C:31]1[O:40][C:34]2=[N:35][CH:36]=[CH:37][C:38]([O:26][C:23]3[CH:24]=[CH:25][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=3)=[C:33]2[CH:32]=1)=[O:30]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 589308884-Chloro-furo[2,3-b]pyridine-2-carboxylic acid methyl ester

Product 1

HCID 589314974-(4-Nitrophenoxy)furo[2,3-b]pyridine-2-carboxylic acid methyl esterYield 4.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

After adding N-methylpyrrolidone (4.0 ml), diisopropylethylamine (1.3 ml) and para-nitrophenol (822 mg) to 4-chlorofuro[2.3-b]pyridine-2-carboxylic acid methyl ester (1.0 g), the mixture was heated and stirred at 140° C. for 5 hours. After cooling, water was added, extraction was performed with ethyl acetate, the organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Tetrahydrofuran was used for recrystallization to obtain the title compound (70 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. extractionextraction
  4. washthe organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customTetrahydrofuran was used for recrystallization

Sources & evidence

ORD record
ord-198c3953f66c491dab3e969c88556efc
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

Loading…