Trifluoroacetic acid → 6-Chloro-4-oxo-1,2,3,4-tetrahydrocarbazole

HRID 1071786Notes

Reaction equation

HRID 1071786 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]N=C2CCCC(=O)C2)=[CH:4][CH:3]=1.F[C:18](F)(F)[C:19]([OH:21])=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][C:2]1[CH2:7][CH2:6][CH2:18][C:19](=[O:21])[C:3]2=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 5224489HCID 5224489, compound

Product 1

HCID 3357036-Chloro-4-oxo-1,2,3,4-tetrahydrocarbazoleYield 42%

Conditions

Temperature
80 °C

Procedure

A mixture of cyclohexane-1,3-dione mono-(4-chlorophenyl) hydrazone (45 mmol) obtained in Example 131 and trifluoroacetic acid (30 mL) is heated to 80° C. for 16 h, cooled to room temperature, poured over ice water and filtered. The filtercake is dried and recrystallized from ethanol/water to afford the title product, 4.2 g (42% yield), identified by HPLC and mass spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customThe filtercake is dried
  4. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-3dfe577c316545c4b56d036a1d47a389
Source dataset
uspto-grants-2005_06
Patent number
US06906095B2

Reaction notes

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