Hydrochloric Acid → 6-[5-(2-Hydroxy-ethylamino)-pyridin-3-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 1774787Notes

Reaction equation

HRID 1774787 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][NH:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[C:21](=[O:27])[CH2:20][CH2:19]3)[CH:13]=[N:14][CH:15]=1)(C)(C)C.Cl.O1CCOCC1>CO>[OH:6][CH2:7][CH2:8][NH:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[C:21](=[O:27])[CH2:20][CH2:19]3)[CH:13]=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 866791516-{5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethylamino]-pyridin-3-yl}-1-methyl-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 715331996-[5-(2-Hydroxy-ethylamino)-pyridin-3-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-oneYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To solution of 6-{5-[2-(tert-butyl-dimethyl-silanyloxy)-ethylamino]-pyridin-3-yl}-1-methyl-3,4-dihydro-1H-quinolin-2-one (0.06 g, 0.146 mmol) in MeOH (2.5 mL) was added 4M HCl in dioxane (0.255 ml, 1.02 mmol) and the reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated in vacuo, the residue dissolved in EtOAc (20 mL) and washed with aq. NaHCO3 (5 mL). The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 2% MeOH(1% NH4OH)-DCM gradient to give the title compound (0.01 g, 22%) as an off white solid. MS: 298.3 (M+H+).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in EtOAc (20 mL)
  3. washwashed with aq. NaHCO3 (5 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by silica gel flash chromatography
  9. washeluting with a 0 to 2% MeOH(1% NH4OH)-DCM gradient

Sources & evidence

ORD record
ord-a8b0723358504177b07681e78dac899d
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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