Methane → HCID 12862351, compound

HRID 904506Notes

Reaction equation

HRID 904506 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:12][CH3:13])=[CH:5][C:6]=1[C:7]([O:9]CC)=O.Cl[C:15]1[N:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=1.C>C(O)(=O)C>[CH2:12]([C:4]1[S:3][C:2]2[N:1]=[C:15]3[CH:16]=[CH:17][C:18]([C:21]([OH:23])=[O:22])=[CH:19][N:20]3[C:7](=[O:9])[C:6]=2[CH:5]=1)[CH3:13]

Participants

5

Reactant 3

HCID 297MethaneHCID 78263Ethyl 2-amino-5-ethyl-3-thenoateHCID 792226-Chloronicotinic acid

Product 1

HCID 12862351HCID 12862351, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-amino-5-ethyl-3-thiophenecarboxylic acid, ethyl ester (Chemische Berichte, Vol. 99, pages 94-100, 1966), 2.0 g (0.01 mol) and 6-chloro-3-pyridinecarboxylic acid (Aldrich Chemical Company), 1.6 g (0.01 mol) is heated in an oil bath at 180°-185° C. for six hours. The mixture is cooled, dissolved in hot glacial acetic acid, activated charcoal (Darco G-60, Matheson, Coleman and Bell) added and the hot suspension filtered through Supercell Hyflo® (Johns-Manville). The filtrate is cooled and 0.33 g of 2-ethyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid is collected; mp 255°-257° C. after recrystallization from methanol.

Workup

  1. temperatureis heated in an oil bath at 180°-185° C. for six hours
  2. temperatureThe mixture is cooled
  3. filtrationthe hot suspension filtered through Supercell Hyflo® (Johns-Manville)
  4. temperatureThe filtrate is cooled
  5. custom0.33 g of 2-ethyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid is collected
  6. custommp 255°-257° C. after recrystallization from methanol

Sources & evidence

ORD record
ord-3bda336f12f04b7a9fbb02eedf671e4c
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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