Methanol → HCID 22722084, compound

HRID 907389Notes

Reaction equation

HRID 907389 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:20]=[CH:19][C:14](C(OC)=O)=[CH:13][N:12]=2)=[CH:5][CH:4]=1.[OH-:21].[Na+].[CH3:23][OH:24]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[C:11]2[N:12]=[CH:13][CH:14]=[CH:19][C:20]=2[C:23]([OH:24])=[O:21])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11129341HCID 11129341, compound

Product 1

HCID 22722084HCID 22722084, compoundYield 78%

Conditions

Temperature
0 °C

Procedure

Methyl 6-[(E)-2-(4-methoxyphenyl)ethenyl]nicotinate (80 mg, 0.297 mmol; see step (i) above) was dissolved in methanol (5 mL) to which sodium hydroxide solution (145 mg in 10 mL water) was added. The reaction mixture was heated under reflux for 3 h. The solvent was removed under partial reduced pressure and the remaining solution was cooled to 0° C. Hydrochloric acid (conc.) was added dropwise with vigorous stirring until pH4 where a precipitate formed. The yellow solid material was collected by filtration, washed with water and dried under reduced pressure at 50° C. to give the title compound (59 mg, 78%).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 3 h
  4. customThe solvent was removed under partial reduced pressure
  5. additionHydrochloric acid (conc.) was added dropwise
  6. customformed
  7. filtrationThe yellow solid material was collected by filtration
  8. washwashed with water
  9. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-57fa9facf9aa457686bcf2e1b61e7f67
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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