3-Hydroxypyridine → 3-Pyridyl 4-(8-cyclohexyloctylamino)benzoate

HRID 903414Notes

Reaction equation

HRID 903414 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.O[C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1>[H-].[Na+].O1CCCC1>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([O:22][C:38]3[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=3)=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 79713-HydroxypyridineHCID 682631,1'-CarbonyldiimidazoleHCID 204757724-(8-Cyclohexyloctylamino)benzoic acid

Product 1

HCID 204757833-Pyridyl 4-(8-cyclohexyloctylamino)benzoate

Reagents, catalysts & solvents 2

HCID 24758Sodium hydrideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 6 g. sample of 4-(8-cyclohexyloctylamino)benzoic acid and 2.7 g. 1,1'-carbonyldiimidazole in 50 ml. dry tetrahydrofuran is stirred for 2 hours. Then, 1.58 g. 3-hydroxypyridine and a trace of sodium hydride catalyst is added and the reaction is refluxed for 3 hours. The solution is cooled, filtered, and evaporated. The product is crystallized from isopropanol.

Workup

  1. temperaturethe reaction is refluxed for 3 hours
  2. temperatureThe solution is cooled
  3. filtrationfiltered
  4. customevaporated
  5. customThe product is crystallized from isopropanol

Sources & evidence

ORD record
ord-5797aaaee66140739934c475e351bc0b
Source dataset
uspto-grants-1980_10
Patent number
US04227014

Reaction notes

Loading…