Methyl 2-(2-fluoro-6-cyanophenyl)-1,6-dihydro-6-oxo-5-phenylnicotinate → Methyl 10-fluoro-4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate

HRID 256699Notes

Reaction equation

HRID 256699 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#N)[C:3]=1[C:10]1[NH:19][C:18](=[O:20])[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]>[Zn].C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[C:10]1=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:16]=[C:17]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:18](=[O:20])[N:19]1[CH2:8]2

Participants

4

Reactant 1

HCID 19785459Methyl 2-(2-fluoro-6-cyanophenyl)-1,6-dihydro-6-oxo-5-phenylnicotinate

Product 1

HCID 18957069Methyl 10-fluoro-4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylateYield 23%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1.04 g of methyl 2-(2-fluoro-6-cyanophenyl)-1,6-dihydro-6-oxo-5-phenylnicotinate, 0.98 g of zinc powder and 30 ml of acetic acid was heated to boiling under reflux for 30 minutes. The mixture was filtered while hot and the filtrate was evaporated in a vacuum. The residue was stirred overnight in 30 ml of water, whereupon the resulting crystals were filtered off under suction and washed with methylene chloride. By chromatography on silica gel with methylene chloride/diethyl ether (9:1) there was obtained yellow crystals which were recrystallized from ethyl acetate. There was obtained 0.23 g of methyl 10-fluoro-4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate with a m.p. of 134°-136°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. filtrationThe mixture was filtered while hot and the filtrate
  4. customwas evaporated in a vacuum
  5. filtrationwere filtered off under suction
  6. washwashed with methylene chloride
  7. customBy chromatography on silica gel with methylene chloride/diethyl ether (9:1) there was obtained yellow crystals which
  8. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6fa08519dc994f95a8a3606dcbd933bc
Source dataset
uspto-grants-1993_11
Patent number
US05258387

Reaction notes

Loading…