Potassium Carbonate → 1-Methylisoquinoline

HRID 494205Notes

Reaction equation

HRID 494205 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-MethylisoquinolineYield 30.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To cooled chlorosulfonic acid (−10° C.) (16 ml) was cautiously added N-(2,2-dimethoxyethyl)-(1-phenyl)ethylamine (D90) (5 g, 0.024 mol) over a period of 2 h. The reaction was allowed to warm to ambient temperature and stirring continued for 3 d. The reaction was then poured into ice-water slurry (500 ml), basified using solid potassium carbonate followed by extraction with DCM. The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo to give the crude product as an oil. Chromatography on silica gel eluting with ethyl acetate afforded the title compound as a yellow oil (1.04 g). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.40 (d, 1H), 8.13 (d, 1H), 7.81 (d, 1H), 7.68 (t, 1H), 7.60 (t, 1H), 7.51 (d, 1H), 2.97 (s, 3H).

Workup

  1. customof 2 h
  2. extractionfollowed by extraction with DCM
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product as an oil

Sources & evidence

ORD record
ord-7f7d23f300c3497e9e2bb32787880ff3
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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