Hydrochloric Acid → 2-[4-(3-Chlorophenyl)-l-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]benzoic acid

HRID 1582985Notes

Reaction equation

HRID 1582985 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH3:20])[C:10](=[O:21])[C:9]=2[C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26]C)=[O:25])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH3:20])[C:10](=[O:21])[C:9]=2[C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([OH:26])=[O:25])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12991197Methyl 2-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]benzoate

Product 1

HCID 129911982-[4-(3-Chlorophenyl)-l-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1.40 g portion of methyl 2-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]benzoate was stirred in 20 ml of methanol and 10 ml of a 1M sodium hydroxide aqueous solution at 60° C. for 15 hours. The reaction mixture was cooled to room temperature and 10 ml of 1M hydrochloric acid was added thereto. The resulting precipitates were collected by filtration and recrystallized from ethyl acetate-diisopropyl ether to obtain 540 mg of 2-[4-(3-chlorophenyl)-l-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]benzoic acid 0.6 hydrate as a colorless crystalline solid.

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-f4e0051ca4c8443d837077dea1993ccc
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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