Hydrochloric Acid → 5-(2-Hydroxy-ethyl)-benzofuran-2-carboxylic acid (2-amino-phenyl)-amide

HRID 1271875Notes

Reaction equation

HRID 1271875 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][OH:28])=[CH:22][C:20]=2[CH:21]=1)=[O:16])(C)(C)C.Cl>C1COCC1.O1CCOCC1>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][OH:28])=[CH:22][C:20]=2[CH:21]=1)=[O:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69487867(2-{[5-(2-Hydroxy-ethyl)-benzofuran-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 104472675-(2-Hydroxy-ethyl)-benzofuran-2-carboxylic acid (2-amino-phenyl)-amideYield 80.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 75 mg (0.189 mmol) (2-{[5-(2-Hydroxy-ethyl)-benzofuran-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester (58) in 3 ml THF were added 1892 μl of 4M solution of HCl in dioxane. The reaction was stirred at 55° C. for 2 h. The solvent was evaporated, ethylacetate was added and the organic phase was washed with saturated aqueous sodium bicarbonate solution and brine and dried over Na2SO4. The solvent was removed to give 45 mg (0.152 mmol) 5-(2-Hydroxy-ethyl)-benzofuran-2-carboxylic acid (2-amino-phenyl)-amide (55); exact MW calc'd [M+H]: 297.12; MW found [M+H]: 297.1.

Workup

  1. customThe solvent was evaporated
  2. additionethylacetate was added
  3. washthe organic phase was washed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-4c544efe695b4887b089e369e3628cb6
Source dataset
uspto-grants-2007_04
Patent number
US07208491B2

Reaction notes

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