[8-(Benzyloxy)-5-chloroquinolin-7-yl]acetaldehyde → 2-[8-(Benzyloxy)-5-chloroquinolin-7-yl]-1-[4-(morpholin-4-ylmethyl)phenyl]ethanol

HRID 551121Notes

Reaction equation

HRID 551121 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]=[O:22])=[CH:11][C:12]([Cl:19])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:23]1([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Mg]Br)=[CH:32][CH:31]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]([C:33]2[CH:32]=[CH:31][C:30]([CH2:29][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[CH:35][CH:34]=2)[OH:22])=[CH:11][C:12]([Cl:19])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 59829696[8-(Benzyloxy)-5-chloroquinolin-7-yl]acetaldehydeHCID 178419631HCID 178419631, compound

Product 1

HCID 671715992-[8-(Benzyloxy)-5-chloroquinolin-7-yl]-1-[4-(morpholin-4-ylmethyl)phenyl]ethanolYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring solution of [8-(benzyloxy)-5-chloroquinolin-7-yl]acetaldehyde (12.50 mmol) in tetrahydrofuran (100 mL) at 0° C. was dropwise added a 0.25M solution of [4-(4-morpholinylmethyl)phenyl]magnesium bromide in tetrahydrofuran (12.50 mmol, 1.0 eq.) and stirring at 0° C. was continued for 30 min. The reaction mixture was then allowed to warm to room temperature and was stirred 20 min then quenched with saturated aqueous sodium bicarbonate solution (100 mL). After stirring 5 min the reaction mixture was extracted with ethyl acetate (3×75 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated to give a thick brown syrup that was purified by column chromatography using 30% acetone/dichloromethane to give the final product as a white solid (1.50 mmol, 12%). MS (ESI) m/z 489.3; HRMS: calcd for C29H29ClN2O3+H+, 489.19395; found (ESI, [M+H]+ Obs'd), 489.1941.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred 20 min
  3. customthen quenched with saturated aqueous sodium bicarbonate solution (100 mL)
  4. stirringAfter stirring 5 min the reaction mixture
  5. extractionwas extracted with ethyl acetate (3×75 mL)
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a thick brown syrup that
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a0ab43bd53a84cbf81a2a2c7936fcbff
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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