Hydrochloric Acid → Methyl 1-oxo-2-(2-oxoethyl)-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616152Notes

Reaction equation

HRID 1616152 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:13]=2)[C:8]1=[O:21].Cl>O1CCCC1.O>[O:21]=[C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=2)[CH:15]=[CH:16][N:7]1[CH2:6][CH:2]=[O:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67283421Methyl 2-(1,3-dioxolan-2-ylmethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Product 1

HCID 86664205Methyl 1-oxo-2-(2-oxoethyl)-1,2-dihydroisoquinoline-7-carboxylateYield 56.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 2-(1,3-dioxolan-2-ylmethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.23 g, 0.8 mmol) in tetrahydrofuran (5 mL) was added 1.0 M hydrochloric acid in water (9.0 mL). The reaction mixture was heated to 65° C. and stirred overnight. The mixture was cooled to rt, water was added and the mixture was extracted with DCM (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (30% to 100% EtOAc/hexanes) to afford methyl 1-oxo-2-(2-oxoethyl)-1,2-dihydroisoquinoline-7-carboxylate (0.11 g, 56%). LC-MS: (FA) ES+ 246.

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionthe mixture was extracted with DCM (2×)
  3. washThe combined organic phases were then washed with water, and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash silica gel chromatography (30% to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4dfdd13f6cb1481bac34bb31e16ca947
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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