Pyridine → 1-(2-acetyl-6-methoxy-1-methyl-2,3,4,9-tetrahydro-1 H-beta-carbolin-9-yl) 1-ethanone

HRID 1004061Notes

Reaction equation

HRID 1004061 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH:16]([CH3:22])[N:15]([C:23](=[O:25])[CH3:24])[CH2:14][CH2:13][C:12]2=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>C1(C)C=CC=CC=1>[C:23]([N:15]1[CH2:14][CH2:13][C:12]2[C:11]3[C:19](=[CH:20][CH:21]=[C:9]([O:8][CH3:7])[CH:10]=3)[N:18]([C:26](=[O:28])[CH3:27])[C:17]=2[CH:16]1[CH3:22])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 18328986HCID 18328986, compound

Product 1

HCID 187942621-(2-acetyl-6-methoxy-1-methyl-2,3,4,9-tetrahydro-1 H-beta-carbolin-9-yl) 1-ethanoneYield 22%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N,N-Diethylaminopyridine (530 mg) and pyridine (1.1 mL) are added to a solution of 1-(6-methoxy-1 -methyl-2,3,4,9-tetrahydro- 1H-β-carbolin-2-yl)-1-ethanone (933 mg) in toluene (100 mL) and acetic anhydride (6 mL). The mixture is refluxed for 48 h. After evaporation of the toluene, the crude product is taken up in water and then extracted with dichloromethane and, after separation on silica gel (chloroform/methanol eluent), the 1-(2-acetyl-6-methoxy-1-methyl-2,3,4,9-tetrahydro-1 H-β-carbolin-9-yl) 1 -ethanone is obtained (22% yield).

Workup

  1. temperatureThe mixture is refluxed for 48 h
  2. customAfter evaporation of the toluene
  3. extractionextracted with dichloromethane
  4. customafter separation on silica gel (chloroform/methanol eluent)

Sources & evidence

ORD record
ord-c85cea1277f74e2c8775ac769915c239
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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