Diphenyl Ether → 1-(2-Methylphenyl)-4-oxo-6-methyl-4,5-dihydropyrrolo[3,2-c]quinoline

HRID 729091Notes

Reaction equation

HRID 729091 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[NH:13][C:12](=[O:22])[C:11]=2[CH2:10][CH2:9]1.C1(OC2C=CC=CC=2)C=CC=CC=1>[Pd].C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[NH:13][C:12](=[O:22])[C:11]=2[CH:10]=[CH:9]1

Participants

5

Reactant 2

HCID 7583Diphenyl EtherHCID 9926017HCID 9926017, compound

Product 1

HCID 157498281-(2-Methylphenyl)-4-oxo-6-methyl-4,5-dihydropyrrolo[3,2-c]quinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-(2-Methylphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline(9.25 g), diphenyl ether (75 ml) and 10% palladium on charcoal (1 g) were heated at reflux for 4 hours, cooled, diluted with ethyl acetate, and filtered through celite. Further dilution with ethyl acetate induced crystallisation of 1-(2-methylphenyl)-4-oxo-6-methyl-4,5-dihydropyrrolo[3,2-c]quinoline (6.68g), m.p. 226°-232°, which was used without further purification.

Workup

  1. temperatureat reflux for 4 hours
  2. temperaturecooled
  3. filtrationfiltered through celite
  4. customcrystallisation of 1-(2-methylphenyl)-4-oxo-6-methyl-4,5-dihydropyrrolo[3,2-c]quinoline (6.68g), m.p. 226°-232°, which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-1fc8691caa634e179565486488a7d64e
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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