Hydrochloric Acid → 1-(4-Fluorophenyl)-1, 4-dihydro-indeno [1, 2-c] pyrazole

HRID 366383Notes

Reaction equation

HRID 366383 reaction equation
O[CH:2]=[C:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=O.Cl.[F:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=1.Cl>C(O)C>[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:4]3[C:5]4[C:10]([CH2:11][C:3]=3[CH:2]=[N:22]2)=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 37648821H-Inden-1-one, 2,3-dihydro-2-(hydroxymethylene)-

Product 1

HCID 122910661-(4-Fluorophenyl)-1, 4-dihydro-indeno [1, 2-c] pyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydroxymethylene indan-1-one, (Example 1(ii) (a) (4.004 g; 250 mmol), p-fluorophenyl hydrazine hydrochloride (Aldrich) (4.106 g; 25.25 mmol) 10M hydrochloric acid (1 cm3) and ethanol (30 cm3), were heated under reflux for 19 hours. After cooling, the solvent was evaporated under reduced pressure, then taken up in dichloromethane and washed with 2M NaOH. The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo. Purification by Kugelrohr distillation (140° C.; 0.01 mmHg) afforded a yellow solid, m.p. 104-105° C.

Workup

  1. temperatureunder reflux for 19 hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated under reduced pressure
  4. washwashed with 2M NaOH
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification
  10. distillationby Kugelrohr distillation (140° C.; 0.01 mmHg)
  11. customafforded a yellow solid, m.p. 104-105° C.

Sources & evidence

ORD record
ord-538bde8ff3034153b72fd8cf2836b91c
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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