Chloroform → N-(7-ethoxy-1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamide

HRID 66789Notes

Reaction equation

HRID 66789 reaction equation
[OH:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH2:7][CH2:8][CH:9]([NH:15][C:16](=[O:18])[CH3:17])[CH2:10][C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[CH2:19](I)[CH3:20].C([O-])([O-])=O.[K+].[K+].C(Cl)(Cl)Cl>O>[CH2:19]([O:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH2:7][CH2:8][CH:9]([NH:15][C:16](=[O:18])[CH3:17])[CH2:10][C:11]=3[NH:12]2)=[CH:4][CH:3]=1)[CH3:20]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 20529233N-(1,3,4,9-tetrahydro-7-hydroxy-2H-carbazol-2-yl)acetamide

Product 1

HCID 20529245N-(7-ethoxy-1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.02 mol of N-(1,3,4,9-tetrahydro-7-hydroxy-2H-carbazol-2-yl)acetamide, 0.022 mol of ethyl iodide, 0.022 mol of anhydrous K2CO3, and 50 ml of Me2CO was stirred and refluxed for 48 hr. Sufficient CHCl3 and H2O were added to the cooled reaction mixture to give two clear layers. The CHCl3 layer was washed with 1 N NaOH, H2O, dried, evaporated, and the resulting solid residue was recrystallized from i-PrOH to give the title compound, mp 184°-186°.

Workup

  1. temperaturerefluxed for 48 hr
  2. customto give two clear layers
  3. washThe CHCl3 layer was washed with 1 N NaOH, H2O
  4. customdried
  5. customevaporated
  6. customthe resulting solid residue was recrystallized from i-PrOH

Sources & evidence

ORD record
ord-50f1e3129a504327ab190b0c9078daf3
Source dataset
uspto-grants-1982_08
Patent number
US04343812

Reaction notes

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