Methyl Acrylate → HCID 64224629, compound

HRID 1483034Notes

Reaction equation

HRID 1483034 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[OH-].[Na+].[C:14]([O:18][CH3:19])(=[O:17])[CH:15]=[CH2:16]>C1COCC1>[O:11]=[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:16][CH2:15][C:14]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 14798Sodium HydroxideHCID 1508963,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 64224629HCID 64224629, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 3,4-dihydroisoquinolin-1(2H)-one (500 mg, 3.40 mmol) in THF (20 mL) and add sodium hydroxide (274.5 mg, 6.79 mmol) followed by methyl acrylate (438.7 mg, 5.10 mmol) in THF (1 mL). Stir the mixture at ambient temperature for 3 hours; quench with water (20 mL); and then dilute with EtOAc (100 mL). Wash the resulting mixture with brine; dry the organic phase over Na2SO4; filter; and concentrate the filtrate under reduced pressure to provide the title compound as a yellow oil (530 mg, 66.9%). MS (m/z): 234 (M+1).

Workup

  1. customquench with water (20 mL)
  2. additionand then dilute with EtOAc (100 mL)
  3. washWash the resulting mixture with brine
  4. dry with materialdry the organic phase over Na2SO4
  5. filtrationfilter
  6. concentrationand concentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-da9d77413918483e9a8230d46c357264
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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