Hydrochloric Acid → HCID 14423302, compound

HRID 1197035Notes

Reaction equation

HRID 1197035 reaction equation
C([O:3][C:4]([CH:6]1[CH2:27][CH2:26][C:9]2[N:10]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[C:11]3[N:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17](=[O:18])[C:8]=2[CH2:7]1)=[O:5])C.[OH-].[K+].C(O)C.Cl>O>[C:4]([CH:6]1[CH2:27][CH2:26][C:9]2[N:10]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[C:11]3[N:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17](=[O:18])[C:8]=2[CH2:7]1)([OH:5])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 14423249HCID 14423249, compound

Product 1

HCID 14423302HCID 14423302, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Saponify 7-ethoxycarbonyl-10-(3-chlorophenyl)-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridin-5(10H)-one (7.1 g) with potassium hydroxide (1.10 g) in a solvent of ethanol and water (142 ml, 9:1 by volume). After 21 hours at 25° C., add water (200 ml), cool the resulting solution in ice, and acidify (pH 2) the solution with concentrated hydrochloric acid. Collect the resulting precipitate on a filter, and crystallize it from ethanol to provide 7-carboxy-10-(3-chlorophenyl)-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridin-5(10H)-one, m.p. 279°-280.5° C.

Workup

  1. temperaturecool the resulting solution in ice
  2. customCollect the resulting precipitate on a filter
  3. customcrystallize it from ethanol

Sources & evidence

ORD record
ord-9e591a0e0ee04b90bed60cc83f829438
Source dataset
uspto-grants-1992_05
Patent number
US05116840

Reaction notes

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