Acetone → Phthalidyl 2-chloro-3-pyridinecarboxylate

HRID 127357

Reaction equation

HRID 127357 reaction equation
CC(C)=O.[Cl:5][C:6]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1.C(N(CC)CC)C.Br[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:25](=[O:26])[O:24]1>O>[Cl:5][C:6]1[C:11]([C:12]([O:14][CH:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:25](=[O:26])[O:24]2)=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 762582-Chloronicotinic acidHCID 962181(3H)-Isobenzofuranone, 3-bromo-

Product 1

HCID 12673421Phthalidyl 2-chloro-3-pyridinecarboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 600 ml of acetone, 31.5 g of 2-chloro-3-pyridinecarboxylic acid is added and suspended by stirring. Triethylamine (40 ml) is added and after 30 minutes 42.6 g of 3-bromophthalide is poured with stirring into the resulting reaction mixture. The mixture is refluxed for 4 hours and then poured into 2000 ml of water at 50° C. To obtain a precipitated compound, the reaction mixture is cooled with continuous stirring. The solid precipitate is collected by filtration, washed with cooled water and then dried under vacuum at a temperature of 40° C. A yield of 38.7 g (67% of theory) of phthalidyl 2-chloro-3-pyridinecarboxylate is obtained (m.p. 137°-8° C.).

Workup

  1. additionis poured
  2. stirringwith stirring into the resulting reaction mixture
  3. temperatureThe mixture is refluxed for 4 hours
  4. customTo obtain a precipitated compound
  5. temperaturethe reaction mixture is cooled with continuous stirring
  6. filtrationThe solid precipitate is collected by filtration
  7. washwashed with cooled water
  8. customdried under vacuum at a temperature of 40° C

Sources & evidence

ORD record
ord-9a92ca4fd2b946499350958549e3da98
Source dataset
uspto-grants-1981_03
Patent number
US04255581

Linked notes

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