Acetic Acid → 6-Fluoro-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid

HRID 1593604Notes

Reaction equation

HRID 1593604 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.[C:10]([OH:13])(=[O:12])[CH3:11]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:8][C:3]1[CH2:4][CH:11]([C:10]([OH:13])=[O:12])[CH2:6][CH2:7][C:2]2=1

Participants

4

Reactant 2

HCID 176Acetic Acid2×HCID 69982(4-Fluorophenyl)hydrazine

Product 1

HCID 214527086-Fluoro-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-fluorophenyhydrazine (0.90 g, 7.14 mmol) was dissolved in glacial acetic acid (25 mL) under a nitrogen atmosphere and added dropwise to a refluxing solution of 3-cyclohexanonecarboxylic acid ethyl ester (1.73 g, 10 mmol) dissolved in glacial acetic acid (15 mL). After the addition was complete, the solution was heated under reflux for 1 hr, cooled to room temperature and allowed to stir overnight. The orange solution was evaporated under reduced pressure to give a yellow-brown solid. The solid was suspended in 10% sulfuric acid and heated under reflux for 5 hrs, cooled to room temperature and allowed to stir overnight. The brown solid was collected by filtration and recrystallized from acetic acid and water to give the compound I (1.21 g), mp: >200° C. MS [M−H]− m/z 232.

Workup

  1. additionAfter the addition
  2. temperaturethe solution was heated
  3. temperatureunder reflux for 1 hr
  4. customThe orange solution was evaporated under reduced pressure
  5. customto give a yellow-brown solid
  6. temperatureheated
  7. temperatureunder reflux for 5 hrs
  8. temperaturecooled to room temperature
  9. stirringto stir overnight
  10. filtrationThe brown solid was collected by filtration
  11. customrecrystallized from acetic acid and water

Sources & evidence

ORD record
ord-252c2a471c264829bce4e2a2a93d4365
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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