7-Nitro-benzofuran-2-carboxylic acid → 7-Nitrobenzofuran

HRID 1487213Notes

Reaction equation

HRID 1487213 reaction equation
[N+:1]([C:4]1[C:12]2[O:11][C:10](C(O)=O)=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]>N1C2C(=CC=CC=2)C=CC=1.O.[Cu]=O>[N+:1]([C:4]1[C:12]2[O:11][CH:10]=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 1

HCID 593413787-Nitro-benzofuran-2-carboxylic acid

Product 1

HCID 112866387-NitrobenzofuranYield 92%

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 962WaterSolventHCID 7047QuinolineSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 7-nitrobenzofuran-2-carboxylic acid (3.54 g, 17.1 mmol) and copper(II) oxide (0.16 g, 2 mmol) in quinoline (30 mL) was heated at 170° C. for 1 hour. Cooling to room temperature, the mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed by brine, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography (petroleum ether/dichloromethane 2/3) to afford the product 7-nitrobenzofuran (2.56 g, yield 92%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.27-8.28 (d, 1H, J=2.0 Hz), 8.12-8.17 (m, 2H), 7.46-7.50 (t, 1H, J=8.0 Hz), 7.215-7.220 (d, 1H, J=2.0 Hz).

Workup

  1. temperatureCooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed by brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. custompurified by silica gel chromatography (petroleum ether/dichloromethane 2/3)

Sources & evidence

ORD record
ord-9c25798f322d4b1a921f98127775a671
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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