Diethyl Ether → (4-Chloroquinolin-7-yl)methanol

HRID 651680Notes

Reaction equation

HRID 651680 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C:9]([Cl:15])=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1)=O.CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:2][CH2:3][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([Cl:15])=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 21708520Methyl 4-chloroquinoline-7-carboxylate

Product 1

HCID 22054610(4-Chloroquinolin-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-45 °C

Procedure

7-Methyloxycarbonyl-4-chloroquinoline (2.1 g, 9.5 mmol) is dissolved in anhydrous THF (25 mL) and anhydrous ether (200 mL). The solution is cooled in a dry ice/acetone bath and treated 1 M lithium aluminum hydride in THF (11.0 mL, 11 mmol). The solution is warmed (approximately −45° C.) for 20 min. and quenched with ethyl acetate. The solution is diluted with ether (100 mL) and treated with water (36 mL), 15% NaOH (36 mL) and water (3×36 mL) in succession. The mixture is filtered and evaporated to yield the title compound as a residue (2.0 g, 9.7 mmol) which is dried under vacuum and used without further purification. MS m/z: M+=193; 1H NMR (CDCl3, 300 MHz) δ0.00, 8.65 (d, 1H), 8.15 (d, 1H), 8.0 (d, 1H), 7.6 (d, 1H), 7.45 (d, 1H), 4.8 (s, 2H).

Workup

  1. temperatureThe solution is cooled in a dry ice/acetone bath
  2. customquenched with ethyl acetate
  3. additionThe solution is diluted with ether (100 mL)
  4. additiontreated with water (36 mL), 15% NaOH (36 mL) and water (3×36 mL) in succession
  5. filtrationThe mixture is filtered
  6. customevaporated

Sources & evidence

ORD record
ord-1c5c37da09e64d2894b14edeb471e77e
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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