Toluene → 7-Quinolinemethanol

HRID 657769

Reaction equation

HRID 657769 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11](OC)=[O:12])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N[C@@H](C1C=NC(C)=CC=1)CCO.C1(C)C=CC=CC=1>O1CCCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][OH:12])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 12554532Methyl quinoline-7-carboxylateHCID 58103597(R)-3-Amino-3-(6-methylpyridin-3-yl)propan-1-ol

Product 1

HCID 976097-Quinolinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Methyl quinoline-7-carboxylate (5 g, 0.01 mol) was dissolved in tetrahydrofuran (40 mL) at −20° C. under an atmosphere of nitrogen. 60% REDAL (60:40, Red-Al(R):toluene, 6.53 mL, 0.0201 mol) was added and allowed to stir at −20° C. for 4 hours. After warming to room temperature, the reaction was quenched slowly with water, concentrated under reduced pressure, partitioned between EtOAc and water, and filtered through Celite. The aqueous phase was extracted with EtOAc. The combined organic layers were dried with MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column to afford the title compound.

Workup

  1. temperatureAfter warming to room temperature
  2. customthe reaction was quenched slowly with water
  3. concentrationconcentrated under reduced pressure
  4. custompartitioned between EtOAc and water
  5. filtrationfiltered through Celite
  6. extractionThe aqueous phase was extracted with EtOAc
  7. dry with materialThe combined organic layers were dried with MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-a29d8a8117d94cc482019a592eb8f544
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Linked notes

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