3-Pyridinecarbonyl chloride, hydrochloride (1:1) → 2,2,10,10-Tetramethylundecane-1,11-diyl dipyridine-3-carboxylate

HRID 1262825Notes

Reaction equation

HRID 1262825 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[CH3:11][C:12]([CH3:27])([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[CH2:23][OH:24])[CH2:13][OH:14]>N1C=CC=CC=1>[C:2]([O:24][CH2:23][C:22]([CH3:26])([CH3:25])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:12]([CH3:27])([CH3:11])[CH2:13][O:14][C:2](=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1

Participants

4

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 2153161,11-Undecanediol, 2,2,10,10-tetramethyl-

Product 1

HCID 30696772,2,10,10-Tetramethylundecane-1,11-diyl dipyridine-3-carboxylateYield 52%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A suspension of 53.10 grams (0.3 mole) of nicotinoyl chloride hydrochloride in 150 ml of anhydrous pyridine was added in 2 hours under stirring with a solution of 12.2 grams (0.05 mole) of 2,2,10,10-tetramethyl-1,11-undecanediol in 30 ml of anhydrous pyridine while keeping the temperature at about 70° C. The reaction was refluxed and stirred for 36 hours then, after cooling, the formed precipitate was removed by filtration. The filtrate was evaporated under vacuum and the obtained residue was treated with a mixture of 200 ml of diethyl ether and 100 ml of an 8% aqueous solution of sodium bicarbonate. The organic layer was separated and washed first with 100 of a 3% aqueous solution of sodium bicarbonate and then with 100 ml of water. After evaporating the diethyl ether in vacuo the obtained residue was dissolved in 50 ml of methylene chloride, the organic solution was twice washed with 30 ml of 1N hydrochloric acid and twice with 50 of water, dried over sodium sulphate and finally brought to dryness. The residue was crystallized from ethanol thus obtaining 11.80 grams of the title product, having m.p. 70°-71° C. Yield: 52% of theoretical.

Workup

  1. additionwas added in 2 hours
  2. customat about 70° C
  3. temperatureThe reaction was refluxed
  4. temperatureafter cooling
  5. customthe formed precipitate was removed by filtration
  6. customThe filtrate was evaporated under vacuum
  7. additionthe obtained residue was treated with a mixture of 200 ml of diethyl ether and 100 ml of an 8% aqueous solution of sodium bicarbonate
  8. customThe organic layer was separated
  9. washwashed first with 100 of a 3% aqueous solution of sodium bicarbonate
  10. customAfter evaporating the diethyl ether in vacuo the obtained residue
  11. dissolutionwas dissolved in 50 ml of methylene chloride
  12. washthe organic solution was twice washed with 30 ml of 1N hydrochloric acid and twice with 50 of water
  13. dry with materialdried over sodium sulphate
  14. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-ed05dabd0ce34b1d856b89d5562ba6e5
Source dataset
uspto-grants-1984_06
Patent number
US04454145

Reaction notes

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