Hydrochloric Acid → 3-Bromo-7-methoxyquinoline

HRID 1627699Notes

Reaction equation

HRID 1627699 reaction equation
[Br:1][CH:2]([CH:5]=O)[CH:3]=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[N:12][C:11]2[C:13]([CH:5]=1)=[CH:14][CH:15]=[C:9]([O:8][CH3:7])[CH:10]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108243-MethoxyanilineHCID 749452-Bromopropanedial

Product 1

HCID 187885483-Bromo-7-methoxyquinolineYield 3.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of bromo-malonaldehyde (10 g, 66.2 mmol) in absolute ethanol (100 mL) was added 3-methoxyaniline (7.3 g, 59.6 mmol). The mixture was heated to 30° C. and stirred at that temperature for 24 h. Conc. HCl (100 mL) was added, and the reaction mixture was heated at 100° C. for two days. After the mixture was concentrated and the residue was partitioned between ethyl acetate (150 mL) and saturated sodium carbonate (50 mL). The organic phase was washed with brine, dried with anhydrous Na2SO4 and concentrated to give a black oil, which was purified by column chromatography (PE/EA=3/1) to give Intermediate 13 as a brown oil (500 mg, 3.8%). MS (ESI): m/z 237.9 [M+1]+.

Workup

  1. temperaturethe reaction mixture was heated at 100° C. for two days
  2. concentrationAfter the mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate (150 mL) and saturated sodium carbonate (50 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried with anhydrous Na2SO4
  6. concentrationconcentrated
  7. customto give a black oil, which
  8. customwas purified by column chromatography (PE/EA=3/1)

Sources & evidence

ORD record
ord-02af9d0ca4ec4432abd82dd93933a138
Source dataset
uspto-grants-2014_07
Patent number
US08785643B2

Reaction notes

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