Quinoline, 3-bromo-8-nitro- → HCID 19592322, compound

HRID 613466Notes

Reaction equation

HRID 613466 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][C:10](Br)=[CH:9]2)([O-:3])=[O:2].[CH2:15]([Sn](CCCC)(CCCC)C=C)[CH2:16]CC>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][C:10]([CH:15]=[CH2:16])=[CH:9]2)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 79286Quinoline, 3-bromo-8-nitro-HCID 81998Tributylvinyltin

Product 1

HCID 19592322HCID 19592322, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 8-nitro-3-bromoquinoline (300 mg), tri-n-butyl(vinyl)tin (491 mg) and tetrakis(triphenylphosphine)palladium(0) (28 mg) in dimethoxyethane (6 ml) was refluxed for 1 hour. The mixture was concentrated in vacuo, and the residue was purified by column chromatography on silica gel (n-hexane-toluene) to give 8-nitro-3-vinylquinoline (127 mg).

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel (n-hexane-toluene)

Sources & evidence

ORD record
ord-c367bb19d7b34f08ab462956dee6c590
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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