6-Chloronicotinic acid → HCID 12862354, compound

HRID 1155861Notes

Reaction equation

HRID 1155861 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:11][CH2:12][CH2:13][CH3:14])=[CH:5][C:6]=1[C:7]([O:9]C)=O.Cl[C:16]1[N:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=1>>[CH2:11]([C:4]1[S:3][C:2]2[N:1]=[C:16]3[CH:17]=[CH:18][C:19]([C:22]([OH:24])=[O:23])=[CH:20][N:21]3[C:7](=[O:9])[C:6]=2[CH:5]=1)[CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 792226-Chloronicotinic acidHCID 11160187HCID 11160187, compound

Product 1

HCID 12862354HCID 12862354, compound

Procedure

A mixture of 2-amino-5-butyl-3-thiophenecarboxylic acid, methyl ester, 21.33 g (0.1 mol) and 6-chloro-3-pyridinecarboxylic acid (Aldrich Chemical Company), 15.76 g (0.1 mol) is heated in a wax bath at 178°-180° C. for one hundred ninety minutes. The mixture is cooled, extracted with hot chloroform and the residue is dissolved in 300 ml of hot glacial acetic acid filtered and 600 ml of hot water added and the mixture stirred on a steam bath for forty minutes and filtered to give 1.23 g of 2-butyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid; mp 250°-252° C. after recrystallization from pyridine.

Workup

  1. temperatureis heated in a wax bath at 178°-180° C. for one hundred ninety minutes
  2. temperatureThe mixture is cooled
  3. extractionextracted with hot chloroform
  4. dissolutionthe residue is dissolved in 300 ml of hot glacial acetic acid
  5. filtrationfiltered
  6. addition600 ml of hot water added
  7. filtrationfiltered

Sources & evidence

ORD record
ord-c780f2dfed3f47e0aed7c39b9d6bf34d
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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