Hydrochloric Acid → 8-(3-(1-(4-Chlorophenyl)-2-(pyridin-4-yl)ethyl)phenyl)-6-isopropylquinoline

HRID 896684Notes

Reaction equation

HRID 896684 reaction equation
C(OC(=O)[CH:5]([C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1)[CH:6]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[C:15]([CH:23]([CH3:25])[CH3:24])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[CH:8]=1)C.[OH-].[Na+].Cl>C1COCC1.CCO.C(OCC)(=O)C>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH:6]([C:7]2[CH:8]=[C:9]([C:13]3[CH:14]=[C:15]([CH:23]([CH3:25])[CH3:24])[CH:16]=[C:17]4[C:22]=3[N:21]=[CH:20][CH:19]=[CH:18]4)[CH:10]=[CH:11][CH:12]=2)[CH2:5][C:33]2[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 208149663-(4-Chloro-phenyl)-3-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-2-pyridin-4-yl-propionic acid ethyl ester

Product 1

HCID 101831968-(3-(1-(4-Chlorophenyl)-2-(pyridin-4-yl)ethyl)phenyl)-6-isopropylquinoline

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the crude ester from Step 3 above in THF/EtOH (10 mL) was added NaOH (2N, 2 mL). The resulting reaction mixture was stirred 18 h at 100° C. then neutralized with HCl 6N to pH 7 and diluted with ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 1:1) provided the 8-{3-[1-(4-chloro-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-6-isopropyl-quinoline compound.

Workup

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with hexane/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-18cb4c5d5fee4d0991dae9e76022921f
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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