Lithium Hydroxide → 3-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-isonicotinic acid

HRID 413696Notes

Reaction equation

HRID 413696 reaction equation
C([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[NH:11][C:12]([O:14][CH2:15][C:16]1[O:17][C:18]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][C:19]=2[CH:20]=1)=[O:13])C.[Li+].[OH-]>C1COCC1>[C:25]1([C:22]2[CH:23]=[CH:24][C:18]3[O:17][C:16]([CH2:15][O:14][C:12]([NH:11][C:6]4[CH:7]=[N:8][CH:9]=[CH:10][C:5]=4[C:4]([OH:31])=[O:3])=[O:13])=[CH:20][C:19]=3[CH:21]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 695624663-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-isonicotinic acid ethyl ester

Product 1

HCID 101348533-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-isonicotinic acidYield 51.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-isonicotinic acid ethyl ester (0.150 g, 0.36 mmol) in THF (3 ml) was added at room temperature 1.0M LiOH (0.72 mL, 0.72 mmol) and the mixture was stirred for 3 h. The solvent was evaporated, water was added, followed by 2N HCl to adjust the pH to 1-2, and the product was extracted with EtOAc. The extract was washed with water, then brine, and dried over magnesium sulfate and concentrated to dryness. Purification by crystallization gave 0.072 g of 3-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-isonicotinic acid as a white solid, mp 235.7-238.9° C.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionthe product was extracted with EtOAc
  4. washThe extract was washed with water
  5. dry with materialbrine, and dried over magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customPurification
  8. customby crystallization

Sources & evidence

ORD record
ord-86ea83f8c55b48d88324de644a1a5045
Source dataset
uspto-grants-2003_05
Patent number
US06569860B2

Reaction notes

Loading…