Ethyl 2-chloro-4-(4-fluorophenyl)quinoline-3-carboxylate → HCID 14780598, compound

HRID 1650135Notes

Reaction equation

HRID 1650135 reaction equation
[Cl:1][C:2]1[C:11]([C:12](OCC)=[O:13])=[C:10]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[Cl:1][C:2]1[C:11]([CH2:12][OH:13])=[C:10]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14780581Ethyl 2-chloro-4-(4-fluorophenyl)quinoline-3-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14780598HCID 14780598, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Ethyl 2-chloro-4-(4-fluorophenyl)-3-quinolinecarboxylate (12.91 g) is dissolved in 200 ml of dichloromethane at -78° C. under an atmosphere of nitrogen. A solution of diisobutylaluminum hydride (DIBAL) (97 ml, 2.5 equivalents) in dichloromethane is added dropwise and the reaction stirred for 3.5 hours at -78° C. The reaction is quenched by addition of a saturated solution of sodium sulfate (20 ml) and removing the cooling bath. The gelatinous mass is filtered through Celite, washed with hot ethyl acetate, and the filtrate evaporated to give 9.36 g of 2-chloro-4-(4-fluorophenyl)-3-quinolinemethanol as a white solid; mp 159°-160° C.; 1H NMR (chloroform-d): δ 8.07 (d, 1H), 7.79-7.70 (m, 1H), 7.53-7.22 (m, 6H), 4.67 (d, 2H), 2.24 (t, 1H) ppm.

Workup

  1. customThe reaction is quenched by addition of a saturated solution of sodium sulfate (20 ml)
  2. customremoving the cooling bath
  3. filtrationThe gelatinous mass is filtered through Celite
  4. washwashed with hot ethyl acetate
  5. customthe filtrate evaporated

Sources & evidence

ORD record
ord-f4f1c3be4d1446049b88c987b0d49298
Source dataset
uspto-grants-1990_05
Patent number
US04923861

Reaction notes

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