Sodium Hydroxide → HCID 70624201, compound

HRID 2420093Notes

Reaction equation

HRID 2420093 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+]>O1CCOCC1.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:11]2[C@@H:16]([OH:17])[CH2:15][CH2:14][CH2:13][NH:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 43013592-(3,4-dimethoxyphenyl)pyridin-3-ol

Product 1

HCID 70624201HCID 70624201, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-(3,4-Dimethoxyphenyl)-3-pyridinol (10.0 g, 43.2 mmoles, described in Example 3) is dissolved in p-dioxane (60 ml) containing 0.1 ml of 12.5N sodium hydroxide. The solution is hydrogenated for 17 hours with Raney nickel catalyst (1.5 g) at 1750 p.s.i. and 140° C. The mixture is filtered and the filtrate is evaporated. The residue is subjected to chromatography on alumina (Woelm, basic activity I) using first chloroform as eluant and then a 1:10 methanol-chloroform solvent combination. The eluates are evaporated, dissolved in acetone and maleic acid is added. The precipitate is crystallized from isopropanol-hexane to give the title compound as the maleate salt, mp 180°-181° C.

Workup

  1. custom140° C
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated
  4. customThe eluates are evaporated
  5. dissolutiondissolved in acetone
  6. additionmaleic acid is added
  7. customThe precipitate is crystallized from isopropanol-hexane

Sources & evidence

ORD record
ord-a0e932321ba548b79e6a6246ec185524
Source dataset
uspto-grants-1978_08
Patent number
US04108997

Reaction notes

Loading…