Ethanol → [5-(4-Fluorophenylcarbamoyl)Pyridin-2-Yloxy]Acetic Acid Ethyl Ester

HRID 859167Notes

Reaction equation

HRID 859167 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:21])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:8][N:7]=1.[CH2:23](O)C>S(=O)(=O)(O)O.C(OCC)(=O)C>[CH2:1]([O:2][C:3](=[O:22])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:21])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:8][N:7]=1)[CH3:23]

Participants

5

Reactant 2

HCID 702EthanolHCID 10402760[5-(4-Fluorophenylcarbamoyl)Pyridin-2-Yloxy]Acetic Acid Methyl Ester

Product 1

HCID 15981316[5-(4-Fluorophenylcarbamoyl)Pyridin-2-Yloxy]Acetic Acid Ethyl EsterYield 20%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [5-(4-fluorophenylcarbamoyl)pyridin-2-yloxy]acetic acid methyl ester (0.030 g, 0.99 mmole), ethanol (2 mL), and sulfuric acid (1 drop) was heated in a sealed tube at 80° C. After 6 h the reaction mixture was poured into ethyl acetate and washed with saturated sodium bicarbonate and dried over sodium sulfate. Removal of the solvents provided 6 mg (20%) of the titled product as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.30 (s 1H), 8.66 (m, 1H), 8.22 (m, 1H), 7.73 (m, 2H), 7.16 (m, 2H), 7.04 (m, 1H), 4.96 (s, 2H); 4.11 (m, 2H); 1.16 (m, 3H); MS (EI) m/z 317.17 (M−H)−.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. customRemoval of the solvents

Sources & evidence

ORD record
ord-3d678e7f49fd4dd29f5ef2300770f20a
Source dataset
uspto-grants-2006_12
Patent number
US07151112B1

Reaction notes

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