Acetic Acid → N-(7-n-butyloxy-1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamide

HRID 126890Notes

Reaction equation

HRID 126890 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([NH:12]N)[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].O=[C:15]1[CH2:20][CH2:19][CH2:18][CH:17]([NH:21][C:22](=[O:24])[CH3:23])[CH2:16]1.CC(O)=O>O>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:9]([C:20]3[CH2:19][CH2:18][CH:17]([NH:21][C:22](=[O:24])[CH3:23])[CH2:16][C:15]=3[NH:12]2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 205292263-n-ButyloxyphenylhydrazineHCID 20529251N-(3-oxocyclohexyl)acetamide

Product 1

HCID 20529247N-(7-n-butyloxy-1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamideYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.2 mol of 3-n-butyloxyphenylhydrazine, 0.2 mol of N-(3-oxocyclohexyl)acetamide, and 350 ml of glacial HOAc was stirred at room temperature for 3 hr and then refluxed for 2 hr. After pouring into 2.5 l of H2O and stirring overnight, the insoluble material had partly crystallized. The crystalline material was filtered, washed with H2O, and dried (23 g, Fraction A). The remaining insoluble semi-solid was taken up in EtOAc, washed with H2O, dried, and evaporated. The dark residue was triturated with Et2O and filtered (b 6.7 g, mp 181°-183°, Fraction B). Additional product was extracted from Fraction A by stirring with two 4 l. portions of Et2O. The combined extracts were evaporated and the resulting residue combined with Fraction B and recrystallized twice from Me2CO to yield 10.2 g of the title compound, mp 182°-184°.

Workup

  1. temperaturerefluxed for 2 hr
  2. stirringstirring overnight
  3. customthe insoluble material had partly crystallized
  4. filtrationThe crystalline material was filtered
  5. washwashed with H2O
  6. customdried (23 g, Fraction A)
  7. washwashed with H2O
  8. customdried
  9. customevaporated
  10. customThe dark residue was triturated with Et2O
  11. filtrationfiltered (b 6.7 g, mp 181°-183°, Fraction B)
  12. extractionAdditional product was extracted from Fraction A
  13. stirringby stirring with two 4 l
  14. customThe combined extracts were evaporated
  15. customrecrystallized twice from Me2CO

Sources & evidence

ORD record
ord-76888315661642e891b23669d52011ad
Source dataset
uspto-grants-1981_03
Patent number
US04254134

Reaction notes

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