4-Fluorophenylhydrazine hydrochloride → 6-FLUORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-3-CARBOXYLIC ACID ETHYL ESTER

HRID 1593608Notes

Reaction equation

HRID 1593608 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[CH2:12][CH2:11][C:9](=O)[CH2:8][CH2:7]1)=[O:5].Cl.[F:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21]N)=[CH:17][CH:16]=1>C(O)C>[CH2:2]([O:3][C:4]([CH:6]1[CH2:12][C:11]2[C:19]3[C:18](=[CH:17][CH:16]=[C:15]([F:14])[CH:20]=3)[NH:21][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 108582426-FLUORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-3-CARBOXYLIC ACID ETHYL ESTERYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Cyclohexanonecarboxylic acid ethyl ester (77 g, 450 mmol) and 4-fluorophenylhydrazine hydrochloride (72 g, 443 mmol) were refluxed in 1.25 L of anhydrous ethanol overnight. The resulting yellow solution was cooled, crystals filtered, the filtrate evaporated, the residue partitioned between ethyl acetate and water, organic layer dried over sodium sulfate, evaporated, crystallized from ethyl acetate/heptane to give 113 g (98%) of the desired product.

Workup

  1. temperatureThe resulting yellow solution was cooled
  2. filtrationcrystals filtered
  3. customthe filtrate evaporated
  4. customthe residue partitioned between ethyl acetate and water, organic layer
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customcrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-a01a9f30e0594e4a9d5052471d886116
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

Loading…