Nicotinic Acid → 3-Pyridinecarbonyl chloride, hydrochloride (1:1)

HRID 2292582Notes

Reaction equation

HRID 2292582 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.S(Cl)([Cl:12])=O>C1(C)C=CC=CC=1>[ClH:12].[C:1]([Cl:12])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 938Nicotinic AcidHCID 24386Thionyl Chloride

Product 1

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.5 g of nicotinic acid were heated to reflux in 1.8 ml of thionyl chloride for one and a half hours. After taking up in toluene and evaporating, the residue was triturated with ether, then dried to obtain 2.12 g of nicotinoyl chloride hydrochloride. 258 mg of the E isomer of Step B of Example 1 were dissolved in 1 ml of pyridine, and 93 mg (0.525 mM) of the freshly prepared nicotinoyl chloride hydrochloride were added and stirred for 2 hours under an inert atmosphere. After diluting with 10 ml of methylene chloride, washing with 1N hydrochloric acid and then with a solution of sodium bicarbonate, drying and evaporating, the residue was chromatographed over silica and eluted with a mixture of methylene chloride and acetone (9-1) to obtain 232 mg of 1,1-dimethylethyl (6S,7S) 7-[2-(2-trityl-aminothiazol-4-yl)-2-(Z)-(methoxyimino)-acetamido]-3-[(3-nicotinoyloxy)-1-(E)propenyl]-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-en-2-carboxylate.

Workup

  1. customevaporating
  2. customthe residue was triturated with ether
  3. customdried

Sources & evidence

ORD record
ord-ede861b0ae3a4566b98e5002f080cae6
Source dataset
uspto-grants-1997_11
Patent number
US05683996

Reaction notes

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