Ammonia → pyrido[3,2-g]quinoline

HRID 1534976Notes

Reaction equation

HRID 1534976 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH:14]=[CH:13][C:12](C(O)=O)=[N:11][C:8]=3[CH:9]=2)[CH:4]=[CH:3][C:2]=1C(O)=O.C(=O)=O.N>COCCOCCO>[N:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH:14]=[CH:13][CH:12]=[N:11][C:8]=3[CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 280Carbon DioxideHCID 13143645Pyrido[3,2-g]quinoline-2,8-dicarboxylic acid

Product 1

HCID 2750235pyrido[3,2-g]quinoline

Reagents, catalysts & solvents 1

HCID 8134Diethylene Glycol Monomethyl EtherSolvent

Conditions

Temperature
165 °C

Procedure

Diethylene glycol monomethyl ether (20 cc) was added to pyrido[3,2-g] quinoline-2,8-dicarboxylic acid (2.01 g, 7.5 mmol) from the above process and cuprous oxide (I) (50 mg, 0.35 mmol), and heated for 5.5 hours at 165° C. Carbon dioxide evolved during the reaction. After the addition of conc. aquous ammonia (25 cc), extracted with dichloromethane (3×100 ml) and dried on potassium carbonate and evaporated dichloromethane to yield pyrido[3,2-g]quinoline.

Workup

  1. extractionextracted with dichloromethane (3×100 ml)
  2. customdried on potassium carbonate
  3. customevaporated dichloromethane

Sources & evidence

ORD record
ord-958bb5393eca46f4a05a7018a97f9e3e
Source dataset
uspto-grants-1992_02
Patent number
US05091535

Reaction notes

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