6-Chloronicotinic acid → HCID 12862350, compound

HRID 1155858Notes

Reaction equation

HRID 1155858 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:12])=[CH:5][C:6]=1[C:7]([O:9]CC)=O.Cl[C:14]1[N:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1>>[CH3:12][C:4]1[S:3][C:2]2[N:1]=[C:14]3[CH:15]=[CH:16][C:17]([C:20]([OH:22])=[O:21])=[CH:18][N:19]3[C:7](=[O:9])[C:6]=2[CH:5]=1

Participants

3

Reactant 2

HCID 792226-Chloronicotinic acidHCID 4062885Ethyl 2-Amino-5-methylthiophene-3-carboxylate

Product 1

HCID 12862350HCID 12862350, compound

Procedure

A mixture of 2-amino-5-methyl-3-thiophenecarboxylic acid, ethyl ester (Chemische Berichte, Vol. 99, pages 94-100, 1966), 18.5 g (0.1 mol) and 6-chloro-3-pyridinecarboxylic acid (Aldrich Chemical Company), 15.7 g (0.1 mol) is heated in an oil bath at 170°-190° C. for 20 hours. The mixture is cooled, extracted with hot chloroform and the residue is dissolved in hot pyridine, cooled and 0.4 g of 2-methyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid is collected; mp 312°-315° C. after recrystallization from methanol.

Workup

  1. temperatureis heated in an oil bath at 170°-190° C. for 20 hours
  2. temperatureThe mixture is cooled
  3. extractionextracted with hot chloroform
  4. dissolutionthe residue is dissolved in hot pyridine
  5. temperaturecooled
  6. custom0.4 g of 2-methyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid is collected
  7. custommp 312°-315° C. after recrystallization from methanol

Sources & evidence

ORD record
ord-d1343413357e4d0c829a63fcedec4005
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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