Hydrochloric Acid → HCID 11645392, compound

HRID 628844Notes

Reaction equation

HRID 628844 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([O:21]CC)=[O:20])[CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>CO>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([OH:21])=[O:20])[CH:13]=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 69234198HCID 69234198, compound

Product 1

HCID 11645392HCID 11645392, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Part C. A solution of ethyl 3-[6-(4-isopropyl-phenyl)-pyridin-2-yl]-benzoate (90 mg) in 3 mL methanol-1 mL water is treated with lithium hydroxide hydrate (50 mg). The solution is heated to between 40 and 50° C. for 12 h. with stirring, then cooled and neutralized to pH 7 with 3 N aq. HCl. The mixture is extracted with ethyl acetate, and the extract is washed with brine, dried over sodium sulfate, filtered and evaporated to afford the title product as a powder (70 mg, 85%), m.p. 215-216° C. NMR (300 MHz, CDCl3): δ 8.86 (1H, s), 8.47 (1H, d, J=8 Hz), 8.18 (1H, d, J=8 Hz), 8.08 (2H, d, J=9 Hz), 7.85 (1H, t, J=7 Hz), 7.77 (1H, d, J=7 Hz), 7.76 (1H, d, J=7 Hz), 7.62 (1H, t, J=8 Hz), 7.38 (2H, d, J=9 Hz), 2.99 (1H, heptet, J=7 Hz), 1.30 (6H, d, J=7 Hz). MS (ES+): m/e 319 (20), 318 (100).

Workup

  1. temperatureThe solution is heated to between 40 and 50° C. for 12 h.
  2. temperaturecooled
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe extract is washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-dcd64888e97546e8b7bf015903c245c4
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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