Sodium Hydroxide → HCID 66835207, compound

HRID 61907Notes

Reaction equation

HRID 61907 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][C:17]=3[O:22]COC)[C:9](=[O:15])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.O1CCOCC1.Cl.[OH-].[Na+]>>[OH:22][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:16]=1[CH:8]1[CH2:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]([CH3:13])([CH3:14])[C:9]1=[O:15]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 204431481,4-Dioxane hydrochlorideHCID 668351667-Methoxy-3-(3-methoxymethoxy-pyridin-4-yl)-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 66835207HCID 66835207, compoundYield 75%

Procedure

Mixture of 7-methoxy-3-(3-methoxymethoxy-pyridin-4-yl)-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound GT15-8, 430 mg) and 4 N hydrochloric acid dioxane solution (5 ml) was heated and stirred at room temperature for 1.5 hrs. The reaction mixture was neutralized with 2 N aqueous solution of sodium hydroxide. The resulting mixture was extracted with the mixture of DCM and MeOH (DCM:MeOH=9:1). The residues obtained after concentration under reduced pressure were purified by silica gel column (DCM/MeOH) to obtain the title compound (280 mg, 75%).

Workup

  1. temperaturewas heated
  2. extractionThe resulting mixture was extracted with the mixture of DCM and MeOH (DCM:MeOH=9:1)
  3. customThe residues obtained
  4. concentrationafter concentration under reduced pressure
  5. customwere purified by silica gel column (DCM/MeOH)

Sources & evidence

ORD record
ord-98563473f5b74177a78db05448f7384f
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

Loading…