6-Chloronicotinic acid → HCID 12862352, compound

HRID 1155860Notes

Reaction equation

HRID 1155860 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:12][CH2:13][CH3:14])=[CH:5][C:6]=1[C:7]([O:9]CC)=O.Cl[C:16]1[N:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=1>>[O:9]=[C:7]1[N:21]2[CH:20]=[C:19]([C:22]([OH:24])=[O:23])[CH:18]=[CH:17][C:16]2=[N:1][C:2]2[S:3][C:4]([CH2:12][CH2:13][CH3:14])=[CH:5][C:6]1=2

Participants

3

Reactant 2

HCID 792226-Chloronicotinic acidHCID 3399457ethyl 2-amino-5-propylthiophene-3-carboxylate

Product 1

HCID 12862352HCID 12862352, compound

Conditions

Temperature
180 °C

Procedure

A mixture of 2-amino-5-propyl-3-thiophenecarboxylic acid, ethyl ester, 7.4 g (0.035 mol) and 6-chloro-3-pyridinecarboxylic acid (Aldrich Chemical Company), 6.4 g (0.041 mol) is heated in an oil bath at 180° C. for two hours. The mixture is cooled, extracted with hot chloroform and the residue is dissolved in hot pyridine, cooled and 0.45 g of 4-oxo-2-propyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid is collected; mp 250°-254° C. after recrystallization from pyridine.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with hot chloroform
  3. dissolutionthe residue is dissolved in hot pyridine
  4. temperaturecooled
  5. custom0.45 g of 4-oxo-2-propyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid is collected
  6. custommp 250°-254° C. after recrystallization from pyridine

Sources & evidence

ORD record
ord-42279cf3a9574bb4896a83d51f3ba361
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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