Hydrochloric Acid → 2-Amino-1-(2-methoxyquinolin-3-yl)ethan-1-one

HRID 2202557Notes

Reaction equation

HRID 2202557 reaction equation
[CH3:1][O:2][C:3]1[C:12]([C:13](=[O:23])[CH2:14][NH:15]C(=O)OC(C)(C)C)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.Cl>O1CCOCC1.C([O-])(O)=O.[Na+]>[NH2:15][CH2:14][C:13]([C:12]1[C:3]([O:2][CH3:1])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 90149566Tert-butyl(2-(2-methoxyquinolin-3-yl)-2-oxoethyl)carbamate

Product 1

HCID 900366552-Amino-1-(2-methoxyquinolin-3-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

F1 was solubilized in dioxane (30 mL) and treated with 16 mL of 4N HCl in dioxane at 0° C. Mixture was stirred for 1 h at room temperature, poured in sat. aq. NaHCO3 and extracted with dichloromethane. The organic phase was dried over Na2SO4, filtered and concentrated to give the title compound which was used as such in the next step. MS (ES+) C12H12N2O2: 217 (M+H)+.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-49682dbf04c044c5bae1f276817298d4
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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