3-Hydroxypyridine → 3-Pyridyl 4-(hexadecylamino)benzoate

HRID 126947

Reaction equation

HRID 126947 reaction equation
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(N1C=CN=C1)(N1C=CN=C1)=O.O[C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1>[H-].[Na+].O1CCCC1>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)=[O:23])=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 79713-HydroxypyridineHCID 472634-(Hexadecylamino)benzoic acidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 234577623-Pyridyl 4-(hexadecylamino)benzoate

Reagents, catalysts & solvents 2

HCID 24758Sodium hydrideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 6 g. (16.6 m moles) sample of 4-(hexadecylamino)-benzoic acid and 2.7 g. (16.6 m moles) 1,1'-carbonyldiimidazole in 50 ml. dry tetrahydrofuran is stirred for 2 hours. Then, 1.58 g. (16.6 m moles) 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-e6f52b2215cc4e8487b9559907b6b9e9
Source dataset
uspto-grants-1981_03
Patent number
US04254138

Linked notes

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