Water → (4-(4-Benzylphenylamino)-6-chloroquinolin-3-yl)methanol

HRID 336869Notes

Reaction equation

HRID 336869 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:25])[CH:23]=3)[N:18]=[CH:17][C:16]=2[C:26](OCC)=[O:27])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1.CCO>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:25])[CH:23]=3)[N:18]=[CH:17][C:16]=2[CH2:26][OH:27])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 58524965Ethyl 4-(4-benzylphenylamino)-6-chloroquinoline-3-carboxylate

Product 1

HCID 58525065(4-(4-Benzylphenylamino)-6-chloroquinolin-3-yl)methanolYield 90.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Ethyl 4-(4-benzylphenylamino)-6-chloroquinoline-3-carboxylate (1.1 g, 2.6 mmol) in THF (13 mL) was added lithium aluminum hydride 2 M solution in THF (4.0 mL, 8.0 mmol) in portions over 10 min at 0° C. The dark brown reaction mixture was stirred at room temperature for 30 min and then treated with 3 mL of water. The resulting solution was dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography using a 95:5 v/v CH2Cl2:EtOH as solvent to afford title compound (880 mg, 88% yield) as a yellow solid.

Workup

  1. dry with materialThe resulting solution was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-cb58702f758b4793a580c63959c66029
Source dataset
uspto-grants-2014_11
Patent number
US08889706B2

Reaction notes

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