Methane → HCID 53966654, compound

HRID 1680440Notes

Reaction equation

HRID 1680440 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][N:6]=1)=[O:4].C>C(O)(C)C.[OH-].[Na+]>[CH2:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1)[CH:13]=[CH:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 297MethaneHCID 53981108HCID 53981108, compound

Product 1

HCID 53966654HCID 53966654, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To the solution of 11.9 g of 5-cinnamylamino-pyridine-2-carboxylic acid methyl ester in 25 ml of isopropanol, 28 ml of 2 N aqueous sodium hydroxide are added and the mixture intermittently heated on the steam bath for 40 minutes. It is cooled, decolorized with charcoal, filtered and the filtrate slightly acidified with hydrochloric acid and acetic acid. The mixture is extracted with benzene, the extract dried, evaporated and the residue recrystallized from benzene/methanol, to yield the 5-cinnamylaminopyridine-2-carboxylic acid melting at 178°-183°.

Workup

  1. temperaturethe mixture intermittently heated on the steam bath for 40 minutes
  2. temperatureIt is cooled
  3. filtrationfiltered
  4. extractionThe mixture is extracted with benzene
  5. customthe extract dried
  6. customevaporated
  7. customthe residue recrystallized from benzene/methanol

Sources & evidence

ORD record
ord-88fd13b4c39a403ba9401421ce2e430b
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

Loading…