Potassium Hydroxide → 7-Nitro-benzofuran-2-carboxylic acid

HRID 1487212Notes

Reaction equation

HRID 1487212 reaction equation
[N+:1]([C:4]1[C:12]2[O:11][C:10]([C:13]([O:15]C)=[O:14])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+]>C(O)C>[N+:1]([C:4]1[C:12]2[O:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68283988HCID 68283988, compound

Product 1

HCID 593413787-Nitro-benzofuran-2-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of methyl 7-nitrobenzofuran-2-carboxylate (4.12 g, 18.6 mmol) in ethanol (100 mL) was added potassium hydroxide (2.08 g, 37.1 mmol). The mixture was heated at reflux for 1 hour, cooled to room temperature and evaporated. The residue was diluted with water, acidified by concentrated hydrochloric acid (12 N). The suspension was stirred for another 30 minutes, and then filtrated. The precipitate was collected, washed with water and dried to afford the product 7-nitrobenzofuran-2-carboxylic acid (3.54 g, yield 92%). 1H NMR (400 MHz, CDCl3) δ ppm 8.28-8.30 (dd, 1H, J=0.8 Hz, 8.0 Hz), 8.06-8.08 (dd, 1H, J=0.8 Hz, 7.6 Hz), 7.641-7.642 (d, 1H, J=0.4 Hz), 7.47-7.51 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customevaporated
  4. additionThe residue was diluted with water
  5. filtrationfiltrated
  6. customThe precipitate was collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-455479f32e1b4331a5781e01182b8152
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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