3-Pyridinemethanol → 4-((Pyridin-3-ylmethoxy)carbonylamino)benzoic acid

HRID 1907749Notes

Reaction equation

HRID 1907749 reaction equation
[N:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][CH:5]=1)=[C:2]=[O:3].[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=1>C1COCC1>[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][C:2]([NH:1][C:4]2[CH:5]=[CH:6][C:7]([C:8]([OH:10])=[O:9])=[CH:13][CH:14]=2)=[O:3])[CH:16]=1

Participants

4

Reactant 2

HCID 75103-PyridinemethanolHCID 589805Ethyl 4-isocyanatobenzoate

Product 1

HCID 597373314-((Pyridin-3-ylmethoxy)carbonylamino)benzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of ethyl 4-isocyanatobenzoate 280 (2.0 g, 10.46 mmol) and pyridin-3-ylmethanol in THF was stirred at room temperature for 18 h then concentrated. The crude material was taken up in 2N HCl, heated to reflux for 16 h then cooled to −78° C. and lyophilized to give a solid material which was triturated with acetone to give title compound 281 (3.098 g, 96% yield).

Workup

  1. concentrationthen concentrated
  2. temperatureheated
  3. temperatureto reflux for 16 h
  4. customto give a solid material which
  5. customwas triturated with acetone

Sources & evidence

ORD record
ord-f6a6850b80ab4c30b7ec4d1d1e15db4c
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

Loading…