Water → HCID 23600236, compound

HRID 709853Notes

Reaction equation

HRID 709853 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) is 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 (ethyl acetate), washed (brine), dried (Na2SO4), filtered and evaporated to dryness to give the crude product, which was purified by silica gel column chromatography (pet. ether:ethyl acetate, 10:1) to give 7-(heptyloxy)quinoline-3-carbaldehyde as yellow solid (610 mg, yield 30%). ESI-MS: 272 (M+H)+.

Workup

  1. extractionextracted (ethyl acetate)
  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 (pet. ether:ethyl acetate, 10:1)

Sources & evidence

ORD record
ord-01143af1e9314a03a2e79443ad925a34
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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