Sodium Hydroxide → Sodium 1-[6-(2-chloro-4-methoxyphenoxy)hexyl]1,4-dihydro-4-oxo-7-methyl-1,8-naphthyridine-3-carboxylate

HRID 232101Notes

Reaction equation

HRID 232101 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]SC1SCC(=O)N=1.[OH:24][C:25]1[C:34]2[C:29](=[N:30][C:31]([CH3:35])=[CH:32][CH:33]=2)[N:28]=[CH:27][C:26]=1[C:36]([OH:38])=[O:37].[OH-].[Na+:40]>CN(C=O)C>[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:28]1[C:29]2[C:34](=[CH:33][CH:32]=[C:31]([CH3:35])[N:30]=2)[C:25](=[O:24])[C:26]([C:36]([O-:38])=[O:37])=[CH:27]1.[Na+:40]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 189218352-{[6-(2-Chloro-4-methoxyphenoxy)hexyl]thio}-4,5-dihydrothiazol-4-oneHCID 178422970HCID 178422970, compound

Product 1

HCID 23671756Sodium 1-[6-(2-chloro-4-methoxyphenoxy)hexyl]1,4-dihydro-4-oxo-7-methyl-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir overnight at room temperature 1 gm. of the iodide prepared in Examples 2 and 3, 10 ml. DMF, 834 mg. 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylic acid and 326 mg. sodium hydroxide in a reaction flask. Wash with water in methylene chloride. Elute on a coarse silica column with methylene chloride then 3% methanol/methylene chloride to isolate the title compound as the carboxylic acid.

Workup

  1. washWash with water in methylene chloride
  2. washElute on a coarse silica column with methylene chloride

Sources & evidence

ORD record
ord-7fffdf6a3f4f41b39a17eb0c77ed5b3c
Source dataset
uspto-grants-1989_07
Patent number
US04851423

Reaction notes

Loading…