Dimethylamine → HCID 86669825, compound

HRID 1620253Notes

Reaction equation

HRID 1620253 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.[CH3:17][NH:18][CH3:19]>O1CCOCC1>[CH3:17][N:18]([CH3:19])[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

Participants

4

Reactant 2

HCID 674DimethylamineHCID 8474006-Chloro-[1,3]dioxolo[4,5-g]quinoline-7-carbaldehyde

Product 1

HCID 86669825HCID 86669825, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

To a stirred solution of 6-chloro-[1,3]dioxolo[4,5-g]quinoline-7-carbaldehyde (1.0 g, 4.07 mmol) in dioxane (10 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added dimethylamine (40% in water, 5.1 mL, 40.7 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 water (30 mL). The precipitate formed was filtered through a fritted glass filter (porosity 3) to give after evaporation 6-(dimethylamino)-[1,3]dioxolo[4,5-g]quinoline-7-carbaldehyde RBO 35166 (960 mg, 97%).

Workup

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed at 40° C. under vacuum
  3. customThe precipitate formed
  4. filtrationwas filtered through a fritted glass
  5. filtrationfilter (porosity 3)
  6. customto give
  7. customafter evaporation 6-(dimethylamino)-[1,3]dioxolo[4,5-g]quinoline-7-carbaldehyde RBO 35166 (960 mg, 97%)

Sources & evidence

ORD record
ord-84602f2ac98a46a1b22393e11745596e
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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