Potassium Carbonate → 1-Methylisoquinoline

HRID 559479Notes

Reaction equation

HRID 559479 reaction equation
ClS(O)(=O)=O.CO[CH:8](OC)[CH2:9][NH:10][CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH3:12][C:11]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24638Chlorosulfonic acidHCID 606869992,2-dimethoxy-N-(1-phenylethyl)ethanamine

Product 1

HCID 155921-Methylisoquinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To cooled chlorosulfonic acid (16 ml, −10° C.) was cautiously added D7 (5 g, 0.024 mol) over a period of 2 h. Reaction was allowed to warm to ambient temperature and stirring continued for 3d. The reaction was then poured into ice-water slurry (500 ml), basified using solid potassium carbonate followed by extraction using DCM. Organic phase was separated, dried over MgSO4, filtered and concentrated under reduced pressure to leave an oil. Chromatography on silica gel eluting with ethyl acetate afforded the title compound as yellow oil.

Workup

  1. customof 2 h
  2. customReaction
  3. extractionfollowed by extraction
  4. customOrganic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto leave an oil

Sources & evidence

ORD record
ord-6f96623406504cfca62cf7790d514dfd
Source dataset
uspto-grants-2011_11
Patent number
US08063078B2

Reaction notes

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