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

HRID 1593606Notes

Reaction equation

HRID 1593606 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 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Cyclohexanonecarboxylic acid ethyl ester (25 g, 0.14 m) and 4-fluorophenyhydrazine hydrochloride (22.5 g, 0.13 m) were dissolved in ethanol (450 mL) and heated under reflux for 16 hrs. After cooling, the white solid was filtered off and the solvent removed under reduced pressure. After partitioning the residue between water and ethyl acetate, the organic portion was separated, dried (MgSO4), and evaporated under reduced pressure to give compound III (35.5 g, 0.13 m). The crude product was recrystallized from heptane. mp: 115-117° C. MS: [M+H]+ @m/e=262. [Lit. ref.: Block, M. H., et al. J. Med. Chem. 2002, 45, 3509].

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hrs
  3. temperatureAfter cooling
  4. filtrationthe white solid was filtered off
  5. customthe solvent removed under reduced pressure
  6. customAfter partitioning the residue between water and ethyl acetate
  7. customthe organic portion was separated
  8. dry with materialdried (MgSO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ca8610ae4a7a4330a622a2450596b29b
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

Loading…