Hydrochloric Acid → HCID 53981108, compound

HRID 1680438Notes

Reaction equation

HRID 1680438 reaction equation
[BH4-].[CH3:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]=[CH:13][CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][N:7]=1)=[O:5].[BH4-].[Na+].Cl>CO.CN(C)C=O.C(O)(=O)C>[CH3:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH:14]=[CH:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:8][N:7]=1)=[O:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 53986343HCID 53986343, compound

Product 1

HCID 53981108HCID 53981108, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To the stirred solution of 8 g of sodim borohydride in 300 ml of methanol the solution of 15 g of 5-cinnamylideneaminopyridine-2-carboxylic acid methyl ester in 60 ml of warm dimethylformamide is added during 1/2 hour while cooling with ice. Simultaneously a 5 g portion and a 3 g portion of sodium borohydride is added and the mixture stirred for 1 hour at 0°. It is warmed to about 20° until dissolution occurs and combined with 18 ml of 12 N hydrochloric acid, 5 ml of acetic acid and 600 ml of ice water. The mixture is cooled to -10°, filtered, the residue washed with water, dried and recrystallized from aqueous methanol, to yield the 5-cinnamylamino-pyridine-2-carboxylic acid methyl ester melting at 131°-133°.

Workup

  1. temperaturewhile cooling with ice
  2. temperatureIt is warmed to about 20° until dissolution
  3. temperatureThe mixture is cooled to -10°
  4. filtrationfiltered
  5. washthe residue washed with water
  6. customdried
  7. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-459f639793904e9daa9a00606c9f78cf
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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