Hydrochloric Acid → 1-(2,4-Dimethoxybenzyl)-6-fluoro-7-(2-furyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 1696910Notes

Reaction equation

HRID 1696910 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([F:21])=[C:13]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)[N:14]=2)[C:9](=[O:22])[C:8]([C:23]([O:25]CC)=[O:24])=[CH:7]1.O.[OH-].[Li+].Cl>C1COCC1.O.[Cl-].[NH4+]>[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([F:21])=[C:13]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)[N:14]=2)[C:9](=[O:22])[C:8]([C:23]([OH:25])=[O:24])=[CH:7]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67275183Ethyl 1-(2,4-dimethoxybenzyl)-6-fluoro-7-(2-furyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 672758741-(2,4-Dimethoxybenzyl)-6-fluoro-7-(2-furyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of EXAMPLE 30A (166 mg) in THF (8 mL) was treated with lithium hydroxide monohydrate (155 mg) in water (7.4 mL), stirred at ambient temperature for 3 hours, diluted with 10% ammonium chloride (20 mL), adjusted to pH 3 with 1M HCl, and extracted with dichloromethane. The extract was dried (Na2SO4), filtered, and concentrated.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe extract was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6197c48e01794bfba8cecf91563b4e96
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

Loading…