Hydrochloric Acid → HCID 64225396, compound

HRID 1483035Notes

Reaction equation

HRID 1483035 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH2:12][CH2:13][C:14]([O:16]C)=[O:15].[OH-].[Li+].Cl.CCOC(C)=O>C1COCC1.CO>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 64224629HCID 64224629, compound

Product 1

HCID 64225396HCID 64225396, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve methyl 3-(1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)propanoate (0.3 g, 1.29 mmol) in THF (12 mL) and MeOH (4 mL). Add lithium hydroxide (0.2 g, 8.23 mmol, in 4 mL H2O). Stir at ambient temperature for 2 hours. Evaporate the solvents from reaction mixture under reduced pressure. Adjust the pH to 5 with 2N HCl. Add EtOAc (60 mL); wash with brine; dry over Na2SO4; filter; and concentrate the filtrate under reduced pressure to provide the title compound (colorless oil, 0.27 g, 95.8%). MS (m/z): 220 (M+1).

Workup

  1. customEvaporate the solvents
  2. customfrom reaction mixture under reduced pressure
  3. washwash with brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationand concentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-ffd93aff8dcc4b79942380b710fa02bb
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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