Sodium Carbonate → HCID 19593040, compound

HRID 613467Notes

Reaction equation

HRID 613467 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[N+:12]([O-:14])=[O:13].[C:15]1(OB(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.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+:12]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[CH:3][C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:11]2)([O-:14])=[O:13]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborate2×HCID 79286Quinoline, 3-bromo-8-nitro-

Product 1

HCID 19593040HCID 19593040, compoundYield 41.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromo-8-nitroquinoline (253 mg), phenylboric acid (159 mg), tetrakis(triphenylphosphine)palladium(0) (23 mg) and aqueous 2M sodium carbonate solution (2.5 ml) in 1,2-dimethoxyethane (3.5 ml) was refluxed for 4 hours. To the mixture was added phenylboric acid (122 mg), and the mixture was additionally refluxed for 3 hours. The resulting mixture, after diluted with ethyl acetate, was washed with aqueous 3° sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by chromatography on silica gel (n-hexane-ethyl acetate) and the obtained oil was crystallized from diethyl ether to give 8-nitro-3-phenylquinoline (104 mg).

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperaturethe mixture was additionally refluxed for 3 hours
  3. washwas washed with aqueous 3° sodium bicarbonate solution and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel (n-hexane-ethyl acetate)
  7. customthe obtained oil was crystallized from diethyl ether

Sources & evidence

ORD record
ord-23455d7ef74a43368bcfeb5956a4bc45
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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