Sodium Hydroxide → HCID 67392233, compound

HRID 907387Notes

Reaction equation

HRID 907387 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][N:12]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:20]=[CH:19][C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67392294HCID 67392294, compound

Product 1

HCID 67392233HCID 67392233, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 6-{(E)-2-[4-(methylsulfanyl)phenyl]ethenyl}nicotinate (80 mg, 0.280 mmol; see step (i) above) was suspended in methanol (4 mL) and a solution of sodium hydroxide (250 mg, in water 10 mL) and the reaction mixture was heated under reflux for 4 h. The solvent was removed under reduced pressure and the aqueous layer was extracted with DCM. The aqueous layer was cooled to 0° C. with ice then HCl(conc.) was added dropwise with stirring until pH4, where a precipitate formed. The solid material was filtered, washed with water and dried under reduced pressure to give the title compound as pale yellow solid (75 mg, 99%).

Workup

  1. temperatureunder reflux for 4 h
  2. customThe solvent was removed under reduced pressure
  3. extractionthe aqueous layer was extracted with DCM
  4. additionHCl(conc.) was added dropwise
  5. customformed
  6. filtrationThe solid material was filtered
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-dfc83d69b20b48a2a13e54983255902d
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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