Hydrochloric Acid → HCID 86669826, compound

HRID 1620255Notes

Reaction equation

HRID 1620255 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[CH:8]=[C:7]3[O:14][CH2:15][O:16][C:6]3=[CH:5][C:4]=2[N:3]=1.[CH2:17]([NH2:19])[CH3:18].Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.C1COCC1>[CH2:17]([NH:19][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[CH:8]=[C:7]3[O:14][CH2:15][O:16][C:6]3=[CH:5][C:4]=2[N:3]=1)[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 516892Sodium BicarbonateHCID 8474006-Chloro-[1,3]dioxolo[4,5-g]quinoline-7-carbaldehyde

Product 1

HCID 86669826HCID 86669826, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 6-chloro-[1,3]dioxolo[4,5-g]quinoline-7-carbaldehyde (1.0 g, 4.24 mmol) in dioxane (10 mL) was added ethylamine (3.58 mL, 70% in water) and the mixture was heated at 160° C. under microwave irradiation for 45 min. After cooling to RT, the mixture was poured into a mixture of THF:1 N HCl aq. solution=1:1 (25 mL) and stirred for 25 min at RT. The mixture was brought to pH=7 with a saturated aq. 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 6-(ethylamino)-[1,3]dioxolo[4,5-g]quinoline-7-carbaldehyde RBO 35180 as a yellow solid (941 mg, 91% 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-e16f2486fbe84223898639d9a9b7cc22
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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