HCID 21449375, compound → HCID 21449367, compound

HRID 597039Notes

Reaction equation

HRID 597039 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][CH:13]3[CH3:21])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1>C1(OC2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:21][C:13]1[N:12]([C:6]2[C:5]3[C:10](=[CH:11][CH:2]=[CH:3][CH:4]=3)[N:9]=[CH:8][CH:7]=2)[C:20]2[C:15]([CH:14]=1)=[CH:16][CH:17]=[CH:18][CH:19]=2

Participants

4

Reactant 1

HCID 21449375HCID 21449375, compound

Product 1

HCID 21449367HCID 21449367, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7583Diphenyl EtherSolvent

Procedure

A solution of 7-chloro-4-(2-methylindolin-1-yl)quinoline (17g.) in diphenyl ether (50ml.) containing 10% w/w palladium on charcoal catalyst (6.5g.) was heated under reflux for 3 hours. The mixture was cooled and filtered, and the solid residue was extracted with hot chloroform (3 × 50ml.; ca 60° C.). The chloroform was evaporated in vacuo from the extract. The residue was chromatographed on a column of chromatographic silica gel (column dimensions: 20 × 3.5cm.) using a 1:3 v/v mixture of diethyl ether and petroleum ether (b.p. 40°-60° C.) as eluant. The solvents were evaporated in vacuo from the eluate to give 4-(2-methylindol-1-yl)quinoline, m.p. 78°-80° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. extractionthe solid residue was extracted with hot chloroform (3 × 50ml.; ca 60° C.)
  6. customThe chloroform was evaporated in vacuo from the extract
  7. customThe residue was chromatographed on a column of chromatographic silica gel (column dimensions: 20 × 3.5cm.)
  8. additiona 1:3 v/v mixture of diethyl ether and petroleum ether (b.p. 40°-60° C.) as eluant
  9. customThe solvents were evaporated in vacuo from the eluate

Sources & evidence

ORD record
ord-059ad3fab74849fc91c5a7e7eaf76e6e
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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