Water → 7-Methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 1727401Notes

Reaction equation

HRID 1727401 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[N-:13]=[N+]=[N-].[Na+].CS(O)(=O)=O.O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][NH:13][C:9]2=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 33557Sodium AzideHCID 3340366-Methoxy-1-Indanone

Product 1

HCID 135216727-Methoxy-3,4-dihydroisoquinolin-1(2H)-oneYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 6-Methoxy-1-indanone (15 g, 92.6 mmol), sodium azide (26.7 g, 277.8 mmol), in CHCl3 was added methane sulfonic acid (60 g, 926 mmol) via addition funnel at 0° C. Reaction mixture was warm to room temperature. Stirring was continued for 3 hr, then poured into cold water. The organics were extracted with methylene chloride and washed with water, sat. NaCl and dried over Na2SO4. Organic solution was concentrated in vacuo and the residue was purified with silica gel eluting with 20% EtOAc/Hexane to give the title compound as a yellow solid (10.5 g, 63%). MS (ES) m/z 178.1.

Workup

  1. additionvia addition funnel at 0° C
  2. customReaction mixture
  3. extractionThe organics were extracted with methylene chloride
  4. washwashed with water, sat. NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationOrganic solution was concentrated in vacuo
  7. customthe residue was purified with silica gel eluting with 20% EtOAc/Hexane

Sources & evidence

ORD record
ord-e1c83b895e6f45ee8b99170edafb19f3
Source dataset
uspto-grants-2009_02
Patent number
US07495111B2

Reaction notes

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