3-Nitrophenylboronic Acid → 6-Isopropyl-8-(3-nitrophenyl)quinoline

HRID 2209487Notes

Reaction equation

HRID 2209487 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[N+:15]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)([O-:17])=[O:16].C([O-])([O-])=O.[Na+].[Na+]>C(O)C.C1C=CC=CC=1>[CH:12]([C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:15]([O-:17])=[O:16])[CH:23]=3)[CH:3]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 218655558-Bromo-6-(propan-2-yl)quinoline

Product 1

HCID 152952666-Isopropyl-8-(3-nitrophenyl)quinolineYield 89.3%

Reagents, catalysts & solvents 1

HCID 21965192Npc112006Solvent

Procedure

8-Bromo-6-isopropylquinoline (1.15 g) was dissolved in 46 mL of ethanol/benzene (1:1). 3-Nitrobenzene boronic acid (1.4 g), Na2CO3 (2M, 9.2 mL) and tetrakistriphenylphosphine palladium (0.23 g) were added successively. The reaction mixture was refluxed for 6 hours and then cooled and concentrated. The resulting residue was partitioned between 75 mL H2O and 100 mL of ethyl acetate, and extracted with ethyl acetate (2×100 mL). The extracts were then dried over MgSO4, filtered, concentrated and chromatographed on silica gel (20:80 ethyl acetate:hexane) yielding 1.2 g of 6-isopropyl-8-(3-nitrophenyl)quinoline as a slightly impure yellow oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe resulting residue was partitioned between 75 mL H2O and 100 mL of ethyl acetate
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. dry with materialThe extracts were then dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed on silica gel (20:80 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-5ec4b421a66f42ba986f107581ba1525
Source dataset
uspto-grants-1995_10
Patent number
US05455252

Reaction notes

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