Methanol → HCID 19381183, compound

HRID 2209496Notes

Reaction equation

HRID 2209496 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](Br)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[N+:13]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14].CO>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:13]([O-:15])=[O:14])[CH:21]=3)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 887MethanolHCID 16773-Nitrophenylboronic AcidHCID 130880438-Bromo-6-methylquinoline

Product 1

HCID 19381183HCID 19381183, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 6-methyl-8-bromoquinoline (1.0 g), 3-nitrobenzene boronic acid (0.63 g), purchased from Lancaster Chemicals, 2M NaCO3 (1.9 mL), methanol (6.5 mL) and benzene 32 mL) was added palladium tetrakis triphenylphosphine (0.47 g) and heated to reflux for 6 hours. The progress of the reaction was monitored by thin-layer chromatography. Upon completion, the reaction mixture was cooled and the solvents removed. Ethyl acetate was added to the residue and the solution was filtered through a pad of Na2SO4. The solution was concentrated and the desired product was purified and isolated by preparative thin-layer chromatography yielding 6-methyl-8-(3-nitrophenyl)quinoline (983 mg) as a yellow oil. Characteristic analytical data are: elemental analysis [calculate (found)] C: 72.72 (72.63), H: 4.58 (4.32), and N: 10.60 (10.72).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hours
  3. temperatureUpon completion, the reaction mixture was cooled
  4. customthe solvents removed
  5. additionEthyl acetate was added to the residue
  6. filtrationthe solution was filtered through a pad of Na2SO4
  7. concentrationThe solution was concentrated
  8. customthe desired product was purified
  9. customisolated by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-465b2c22994d439e99a393bcf2f5bfb4
Source dataset
uspto-grants-1995_10
Patent number
US05455252

Reaction notes

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