Triphenylphosphine → HCID 19592729, compound

HRID 613533Notes

Reaction equation

HRID 613533 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH2:17][CH3:18])=[C:12]2[CH2:19][CH2:20]O)=[O:5].[Br:27]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:27][CH2:20][CH2:19][C:12]1[C:11]2[C:16](=[C:7]([NH:6][C:4](=[O:5])[C:3]3[C:2]([Cl:1])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:26])[CH:8]=[CH:9][CH:10]=2)[N:15]=[CH:14][C:13]=1[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 19592302HCID 19592302, compound

Product 1

HCID 19592729HCID 19592729, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(2,6-dichlorobenzoylamino)-3-ethyl-4-(2-hydroxyethyl)quinoline (405 mg) in dichloromethane were added N-bromosuccinimide (241 mg) and triphenylphosphine (355 mg) under water cooling, and the mixture was stirred for 30 minutes at the same temperature. The mixture was concentrated in vacuo, and the residue was purified by column chromatography on silica gel (dichloromethane) and crystallized from n-hexane to give 4-(2-bromoethyl)-8-(2,6-dichlorobenzoylamino)-3-ethylquinoline (424 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel (dichloromethane)
  3. customcrystallized from n-hexane

Sources & evidence

ORD record
ord-2e2f924f456b47ccb9f40eb3ab4ab205
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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