Butylamine → Butyl (4-chloroquinolin-6-ylmethylene)-amine

HRID 853007Notes

Reaction equation

HRID 853007 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=O)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:14]([NH2:18])[CH2:15][CH2:16][CH3:17].C1COCC1>C(OCC)(=O)C>[CH2:14]([N:18]=[CH:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][CH:3]=[C:2]2[Cl:1])[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 8028TetrahydrofuranHCID 534172264-Chloroquinoline-6-carbaldehyde

Product 1

HCID 58615380Butyl (4-chloroquinolin-6-ylmethylene)-amineYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-chloro-quinoline-6-carbaldehyde (3.59 g, 18.73 mmol) in heptanes (36 mL) was added n-butylamine(1.51 g, 20.60 mmol, 1.1 equiv.) at room temperature. The reaction mixture was stirred for 5 h at room temperature by this time all solids were dissolved and gave a light brown solution containing a little oily stuff on the wall of flask. Then, 4 mL of THF was added and the clear solution was stirred for another 15 h. This solution was diluted with ethyl acetate (50 mL) and washed with brine solution and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solvents were removed under the vacuum and the remaining residue was dried under high vacuum to afford 4.62 g (˜100% yield) of butyl (4-chloro-quinolin-6-ylmethylene)-amine as a brown oil which was used directly for the next substitution reaction. LRMS(+) m/e calcd for C14H15ClN2 (M+H)+247.7, found 247.2.

Workup

  1. dissolutionwere dissolved
  2. customgave a light brown solution
  3. additioncontaining a little oily stuff on the wall of flask
  4. stirringthe clear solution was stirred for another 15 h
  5. washwashed with brine solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration of the drying agent
  8. customthe solvents were removed under the vacuum
  9. customthe remaining residue was dried under high vacuum

Sources & evidence

ORD record
ord-5668e3213f134148a6ab76af18e99724
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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