Hydrochloric Acid → HCID 11536983, compound

HRID 628839Notes

Reaction equation

HRID 628839 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([O:21]CC)=[O:20])[CH:13]=[N:14][CH:15]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>CO.O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[C:12]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([OH:21])=[O:20])[CH:13]=[N:14][CH:15]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 69234812HCID 69234812, compound

Product 1

HCID 11536983HCID 11536983, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
45 °C

Procedure

Part C. A solution of ethyl 3-[5-(4-isopropyl-phenyl)-pyridin-3-yl]-benzoate (100 mg) in methanol-water (3 mL/1 mL) is treated with lithium hydroxide hydrate (50 mg), and the solution is heated to 40-50° C. for 12 h. After cooling, the solution is neutralized to pH 7 with 3 N HCl and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, filtered and evaporated to afford the title compound as a powder (80 mg, 87%), m.p. 155-156° C. 1H NMR (300 MHz, CDCl3): δ 8.93-8.90 (2H, m), 8.44 (1H, s), 8.21-8.19 (2H, m), 7.89 (1H, d, J=7 Hz), 7.64 (1H, t, J=8 Hz), 7.61 (2H, d, J=9 Hz), 7.39 (2H, d, J=9 Hz), 3.00 (1H, heptet, J=7 Hz), 1.30 (6H, d, J=7 Hz). MS (ES+): m/e 319 (22), 318 (100).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-53f4a9b903fe4e98a84feb9909601eab
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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