Hydrochloric Acid → HCID 15592451, compound

HRID 1263230Notes

Reaction equation

HRID 1263230 reaction equation
[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2=[C:12]3[C:17](=[CH:18][C:7]4=[C:8]2[N:3]1[CH2:4][CH:5]([C:20]([O:22]CC)=[O:21])[C:6]4=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13]3.[OH-].[K+].CC1CCC2=C3C(=CC4=C2N1CC(C([O-])=O)C4=O)C=CC=C3.[K+].Cl>C(O)C.O>[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2=[C:12]3[C:17](=[CH:18][C:7]4=[C:8]2[N:3]1[CH2:4][CH:5]([C:20]([OH:22])=[O:21])[C:6]4=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13]3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15592450HCID 15592450, compoundHCID 23677347HCID 23677347, compound

Product 1

HCID 15592451HCID 15592451, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of ethyl 1,2-dihydro-3-methyl-7-oxo-3H,5H-naptho[1,2,3-ij]quinolizine-6-carboxylate (12.5 g., 0.0389 mole) in ethanol (175 ml.) was treated with a solution of potassium hydroxide (4.3 g., 0.0786 mole) in ethanol (175 ml.). The mixture was then heated to its reflux temperature and maintained at reflux for two hours. The intermediate formed was potassium 1,2-dihydro-3-methyl-7-oxo-3H,5H-naphtho[1,2,3-ij]quinolizine-6-carboxylate. The mixture was diluted with hot water (350 ml.) then acidified with hydrochloric acid. The precipitate was collected by filtration, washed with a fifty percent ethanol-water mixture and dried. The solid was recrystallized from N,N-dimethylformamide to give yellow needles of 1,2-dihydro-3-methyl-7-oxo-3H,5H-naphtho[1,2,3-ij]quinolizine-6-carboxylic acid, m.p. 270°-273° C.

Workup

  1. temperatureThe mixture was then heated to its
  2. temperaturereflux temperature
  3. temperaturemaintained
  4. temperatureat reflux for two hours
  5. customThe intermediate formed
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with a fifty percent ethanol-water mixture
  8. customdried
  9. customThe solid was recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-ab3e20e694924e248998a4e8bf784a81
Source dataset
uspto-grants-1984_06
Patent number
US04456606

Reaction notes

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