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

HRID 126892Notes

Reaction equation

HRID 126892 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-9c73945c65274a80b3d8e1aaa760b5f1
Source dataset
uspto-grants-1981_03
Patent number
US04254134

Reaction notes

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