3-Benzyl-7-chloroquinoline-2-carbaldehyde → 1-(3-Benzyl-7-chloroquinolin-2-yl)-2-methylpropan-1-ol

HRID 271832

Reaction equation

HRID 271832 reaction equation
[CH2:1]([C:8]1[C:9]([CH:19]=[O:20])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([Cl:18])[CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21]([Mg]Cl)([CH3:23])[CH3:22]>C(Cl)Cl>[CH2:1]([C:8]1[C:9]([CH:19]([OH:20])[CH:21]([CH3:23])[CH3:22])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([Cl:18])[CH:12]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 598361973-Benzyl-7-chloroquinoline-2-carbaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 598361911-(3-Benzyl-7-chloroquinolin-2-yl)-2-methylpropan-1-olYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-benzyl-7-chloroquinoline-2-carbaldehyde (1.23 g, 4.4 mmol) in anhydrous DCM (12 ml) at −78° C., was added isopropylmagnesium chloride (6.6 m, 13.2 mmol). The resulting solution was allowed to warm to ambient temperature over one hour. The reaction mixture was then quenched with saturated NH4Cl and extracted with DCM (3×). The combined organic layers were washed with brine, dried over MgSO4, and the solvent was removed in vacuo. The crude product was subjected to flash column chromatography using an ISCO purification system. Elution in hexanes with a gradient of ethyl acetate (0-100%) yielded 1-(3-benzyl-7-chloroquinolin-2-yl)-2-methylpropan-1-ol 25 (0.44 g, 1.3 mmol, 30%) as a red oil.

Workup

  1. customThe reaction mixture was then quenched with saturated NH4Cl
  2. extractionextracted with DCM (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customan ISCO purification system
  7. washElution in hexanes with a gradient of ethyl acetate (0-100%)

Sources & evidence

ORD record
ord-38bebffedd004238a9d7d4ab96442a31
Source dataset
uspto-grants-2008_11
Patent number
US07452996B2

Linked notes

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