Methanesulfonic Acid → HCID 66835135, compound

HRID 61908Notes

Reaction equation

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

Participants

Reactant 3

HCID 6395Methanesulfonic Acid

HCID 14798Sodium Hydroxide

HCID 66835207HCID 66835207, compound

Product 1

HCID 66835135HCID 66835135, compoundYield 43.4%

Conditions

Temperature: 110 °C

Procedure

Mixture of 3-(3-hydroxy-pyridin-4-yl)-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound GT15-9, 270 mg) and methanesulfonic acid (1 ml) was stirred and heated at 110° C. for 0.5 hrs. After cooling, 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 organic layer was concentrated under reduced pressure, and the resulting residues were purified by silica gel column (DCM/MeOH) to obtain the title compound (110 mg, 43%).

Workup

temperatureAfter cooling
extractionThe resulting mixture was extracted with the mixture of DCM and MeOH (DCM:MeOH=9:1)
concentrationThe organic layer was concentrated under reduced pressure
customthe resulting residues were purified by silica gel column (DCM/MeOH)

Sources & evidence

ORD record: ord-1cff5ac194c84d2d9c7ba131a54a0b7d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Reaction notes

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