HCID 23600236, compound → HCID 67407596, compound

HRID 709897Notes

Reaction equation

HRID 709897 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([CH:19]=[O:20])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:21][Mg]I>C1COCC1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([CH:19]([OH:20])[CH3:21])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 23600236HCID 23600236, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 67407596HCID 67407596, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(heptyloxy)quinoline-3-carbaldehyde (1.6 g, 5.9 mmol) in THF (30 mL) at 0° C. was added CH3MgI (2 g, 12 mmol, 2 eq.) dropwise over 10 min. The mixture was warmed to rt over 8 h. Then, the reaction mixture was quenched (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, 1:5) to give desired compound as yellow oil (1.35 g, yield 80%). ESI-MS: 288 (M+H)+. 1H NMR (300 MHz, CDCl3) δ: 0.90 (t, 3H), 1.32-1.41 (m, 6H), 1.43-1.49 (m, 2H), 1.56-1.58 (d, 2H), 1.78-1.85 (m, 2H), 4.02 (t, 2H), 5.02-5.07 (q, 1H), 7.14-7.17 (m, 1H), 7.36 (s, 1H), 7.60-7.63 (d, 1H), 8.01 (s, 1H), 8.72 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-ca8da881a8e2465984d45b1166a85a08
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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