Sodium Hydroxide → HCID 66603822, compound

HRID 1627864Notes

Reaction equation

HRID 1627864 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C:3]=1[CH:23]([CH2:28][CH2:29][CH3:30])[C:24]([O:26]C)=[O:25].[OH-].[Na+]>CO.O>[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[C:3]=1[CH:23]([CH2:28][CH2:29][CH3:30])[C:24]([OH:26])=[O:25]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 49805718HCID 49805718, compound

Product 1

HCID 66603822HCID 66603822, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl [2-methyl-4-(p-tolyl)-5H-cyclohepta[4,5]thieno [2,3-b]pyridin-3-yl]pentanoate (0.434 g; 1.03 mmol) in methanol (10 mL) and water (1 mL), was added a solution of sodium hydroxide 10 N (1 mL) and the mixture was heated at 60° C. for 18 h. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the mixture was acidified with HCl (1N) until pH 1. The organic layer was washed with brine, water, dried over magnesium sulphate and concentrated under reduced pressure. The crude residue was crystallized from a mixture ethyl acetate-heptane to furnish 0.38 g (90%) of the title compound as a light yellow solid.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with brine, water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was crystallized from a mixture ethyl acetate-heptane

Sources & evidence

ORD record
ord-5865a1c03a6842f2b235f8c742f1d1ce
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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