Epichlorohydrin → 3,4-Dihydro-5-(2-oxiranylmethoxy)-1(2H)-isoquinolinone

HRID 1645897Notes

Reaction equation

HRID 1645897 reaction equation
C[O-].[Na+].[Na].[OH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][NH:10][C:11]2=[O:16].[CH2:17]([CH:19]1[O:21][CH2:20]1)Cl>CO>[O:21]1[CH2:20][CH:19]1[CH2:17][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][NH:10][C:11]2=[O:16]

Participants

6

Reactant 4

HCID 7835Epichlorohydrin2×HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 132366635-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 232893633,4-Dihydro-5-(2-oxiranylmethoxy)-1(2H)-isoquinolinoneYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium methoxide (made from 2.4 g (106 mmol) of sodium) in 360 ml of methanol was added 14.5 g (106 mmol) of 3,4-dihydro-5-hydroxy-1(2H)-isoquinolinone. Then 22.2 g of epichlorohydrin in 250 ml of methanol was added dropwise at 55°. After 18 hours an additional 5 g of epichlorohydrin was added and the mixture was stirred for two hours more. The reaction was cooled and concentrated. The residue was chromatographed (SiO2, chloroform/methanol 8:1) to provide 7.9 g (34%) of the desired product. An analytical sample was obtained by recrystallization from chloroform; mp 165°-166°.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customThe residue was chromatographed (SiO2, chloroform/methanol 8:1)

Sources & evidence

ORD record
ord-ff85abc7f4944d65acc2bbe12a8ba694
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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