Sodium hydroxide ethanol → 6-Iodoquinoxaline-2-carboxylic acid

HRID 2273626Notes

Reaction equation

HRID 2273626 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([O:14]CC)=[O:13])[CH:6]=[N:5]2.[OH-].[Na+].C(O)C>C(O)(=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[N:5]2

Participants

4

Reactant 2

HCID 23692425Sodium hydroxide ethanolHCID 53485588Ethyl 6-iodoquinoxaline-2-carboxylate

Product 1

HCID 581520206-Iodoquinoxaline-2-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of compound 9 (1.30 g, 3.96 mmol) in a 2.0 N sodium hydroxide/ethanol solution (1/1, v/v, 6 mL) was refluxed for 30 min. After cooling to room temperature, the reaction mixture was acidified (pH=4-5) with acetic acid and cooled to 0° C. The resulting precipitate was removed by filtration and dried in a vacuum oven to afford acid 23 (1.08 g, 3.29 mmol) as a white solid. Yield 91%; mp 242-244° C.; 1H NMR (200 MHz, DMSO-d6) δ 7.97 (d, 1H, J=8 Hz), 8.15 (d, 1H, J=8 Hz), 8.52 (s, 1H), 9.36 (s, 1H); ESI-MS m/z 298.6 [M−H]−.

Workup

  1. temperaturecooled to 0° C
  2. customThe resulting precipitate was removed by filtration
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-96c2f833406e4fe2985535c3e6cc06cd
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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