Water → HCID 23600236, compound

HRID 709896Notes

Reaction equation

HRID 709896 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH:12]=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:15]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH:12]=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 123691-BromoheptaneHCID 1356489667-Hydroxy-3-quinolinecarbaldehyde

Product 1

HCID 23600236HCID 23600236, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7-hydroxyquinoline-3-carbaldehyde (1.3 g, 7.5 mmol) in DMF (30 mL) was added 1-bromo-heptane (5.37 g, 30 mmol, 4 eq.) and K2CO3 (2.0 g, 15 mmol, 2 eq.). The mixture was warmed to 60° C. over 3 h. Then, the reaction mixture was diluted (water), extracted (EA), washed (brine), dried (Na2SO4), filtered and evaporated to dryness to give the crude product, which was purified by silica gel column chromatography (PE-EA, 10:1) to give desired compound as yellow solid (610 mg, yield 30%). ESI-MS: 272 (M+H)+. 1H NMR (300 MHz, CDCl3) δ: 0.90 (t, 3H), 1.252 (s, 3H), 1.32-1.48 (m, 6H), 1.50-1.54 (m, 2H), 1.84-1.91 (m, 2H), 4.15 (t, 2H), 7.27-7.29 (m, 1H), 7.454 (s, 1H), 7.828-7.851 (d, 1H), 8.506 (s, 1H), 9.286 (s, 1H), 10.17 (s, 1H).

Workup

  1. extractionextracted (EA)
  2. washwashed (brine)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto give the crude product, which
  7. customwas purified by silica gel column chromatography (PE-EA, 10:1)

Sources & evidence

ORD record
ord-3dc91530731e4db5bf4ce006a51d1cc3
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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