Dimethylamine → 2-(Dimethylamino)-6-methylquinoline-3-carbaldehyde

HRID 1620192Notes

Reaction equation

HRID 1620192 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7](OC)[CH:8]=2)[N:3]=1.[CH3:16][NH:17][CH3:18].O1CCOC[CH2:20]1>>[CH3:16][N:17]([CH3:18])[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:20])[CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 312751,4-DioxaneHCID 6890792-Chloro-6-methoxyquinoline-3-carbaldehyde

Product 1

HCID 866698152-(Dimethylamino)-6-methylquinoline-3-carbaldehydeYield 95%

Conditions

Temperature
160 °C

Procedure

To a stirred solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (1.0 g, 4.86 mmol) in dioxane (10 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added dimethylamine (40% in water, 6.1 mL, 48.6 mmol) and the reaction mixture was stirred for 45 min at 160° C. under microwave irradiation. After cooling to RT, the volatiles were removed at 40° C. under vacuum and the resulting yellow oil was taken back in CH2Cl2 (30 mL). The organic layer was washed with water (3×20 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated under vacuum to give 2-(dimethylamino)-6-methylquinoline-3-carbaldehyde RBO 35148 as a yellow oil (988 mg, 95% yield).

Workup

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed at 40° C. under vacuum
  3. washThe organic layer was washed with water (3×20 mL), brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-40a9a67b7e87479eaa5d92cac7dfabe0
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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