Hydrochloric Acid → 6-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid

HRID 1817303Notes

Reaction equation

HRID 1817303 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([C:17]([O:19]CC)=[O:18])=[N:12][CH:11]=[C:10]([O:22][CH3:23])[C:9]=3[C:8]2=[O:24])=[CH:4][CH:3]=1.[OH-].[Li+].Cl>CO.O.C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([C:17]([OH:19])=[O:18])=[N:12][CH:11]=[C:10]([O:22][CH3:23])[C:9]=3[C:8]2=[O:24])=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69058090Ethyl 6-(4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

Product 1

HCID 690589806-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-(4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (1.21 g, 3.38 mmol) in methanol (5 mL) and water (5 mL) and THF (5 mL) was added lithium hydroxide (0.425 g, 10.13 mmol). After 5 minutes, 1N HCl (3 equiv.) was added to the product mixture, which was then dried under vacuum to provide the crude title compound.

Workup

  1. customwas then dried under vacuum

Sources & evidence

ORD record
ord-ca77686f9762421386073e017e2fdde6
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

Loading…