6-Chloronicotinic acid → HCID 12953061, compound

HRID 1155899Notes

Reaction equation

HRID 1155899 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=O)=[C:4]([CH3:8])[S:5][C:6]=1[CH3:7].Cl[C:14]1[N:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1>CO>[CH3:8][C:4]1[S:5][C:6]([CH3:7])=[C:2]2[C:3]=1[C:9](=[O:11])[N:19]1[CH:18]=[C:17]([C:20]([OH:22])=[O:21])[CH:16]=[CH:15][C:14]1=[N:1]2

Participants

4

Reactant 2

HCID 792226-Chloronicotinic acidHCID 11019562Methyl 4-amino-2,5-dimethylthiophene-3-carboxylate

Product 1

HCID 12953061HCID 12953061, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 18.5 g (0.1 mol) of 4-amino-2,5-dimethyl-3-thiophenecarboxylic acid, methyl ester and 15.76 g (0.1 mol) of 6-chloro-3-pyridinecarboxylic acid (Aldrich Chemical Company) is heated in a wax bath at 168°-186° C. for one hundred ten minutes and then at 185°-186° C. for ninety minutes under nitrogen. The mixture is cooled, suspended in hot methanol, cooled and 4.2 g of crude product is collected. This material is dissolved in hot pyridine, activated charcoal (Darco-G60, Matheson, Coleman and Bell) is added and the hot suspension is filtered through Supercell Hyflo® (Johns-Manville). The filtrate is cooled to give 1.75 g of 1,3-dimethyl-10-oxo-10H-pyrido[1,2-a]thieno[3,4-d]pyrimidine-7-carboxylic acid; mp 336° C. (dec) after recrystallization from pyridine.

Workup

  1. temperatureis heated in a wax bath at 168°-186° C. for one hundred ten minutes
  2. waitat 185°-186° C. for ninety minutes under nitrogen
  3. temperatureThe mixture is cooled
  4. temperaturecooled
  5. custom4.2 g of crude product is collected
  6. dissolutionThis material is dissolved in hot pyridine
  7. additionactivated charcoal (Darco-G60, Matheson, Coleman and Bell) is added
  8. filtrationthe hot suspension is filtered through Supercell Hyflo® (Johns-Manville)
  9. temperatureThe filtrate is cooled

Sources & evidence

ORD record
ord-34a3b1578f9143f284654b841c55ffbe
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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