Hydrochloric Acid → 2-(Ethylamino)-6-methylquinoline-3-carbaldehyde

HRID 1620190Notes

Reaction equation

HRID 1620190 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]([CH3:14])[CH:8]=2)[N:3]=1.[CH2:15]([NH2:17])[CH3:16].Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.C1COCC1>[CH2:15]([NH:17][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:14])[CH:8]=2)[N:3]=1)[CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 516892Sodium BicarbonateHCID 6890812-Chloro-6-methylquinoline-3-carboxaldehyde

Product 1

HCID 866698142-(Ethylamino)-6-methylquinoline-3-carbaldehydeYield 54%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 2-chloro-6-methylquinoline-3-carbaldehyde (1.0 g, 4.86 mmol) in dioxane (10 mL) in a 20 mL microwave vial was added ethylamine (4 mL, 70% in water) and the resulting mixture was heated at 160° C. under microwave irradiation for 45 min. After cooling to RT, the mixture was poured into a solution THF:1 N HCl=1:1 (25 mL) and stirred for 25 min at RT. The mixture was neutralized until pH=7 with a saturated solution of NaHCO3 and extracted with CH2Cl2 (50 mL). The organic layer was washed with H2O (3×30 mL), brine (30 mL), dried over Na2SO4, filtered and evaporated to give 2-(ethylamino)-6-methylquinoline-3-carbaldehyde RBO 35156 as a yellow solid (566 mg, 54% yield).

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with CH2Cl2 (50 mL)
  3. washThe organic layer was washed with H2O (3×30 mL), brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3bc894ac6a634241ac38615017deb3fb
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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