Sodium borohydride → HCID 53773077, compound

HRID 1680444Notes

Reaction equation

HRID 1680444 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[CH:7][N:6]=1)=[O:4].[BH4-].[Na+]>CN(C)C=O.CO>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 53820628HCID 53820628, compound

Product 1

HCID 53773077HCID 53773077, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

The solution of 18.6 g of 5-(m-fluorobenzylideneamino)-pyridine-2-carboxylic acid methyl ester in 50 ml of hot dimethylformamide is added all at once to the solution of 5.0 g of sodium borohydride in 230 ml of methanol at -20° while stirring. The mixture warms to approximately 0° and after one hour the mixture is warmed to 35° for 10-15 minutes. It is cooled, one-half of the methanol is distilled off and the cold concentrate is conbined with 2 ml of acetic acid and the solution of 9 ml of 12 N hydrochloric acid in 70 ml of ice water. The clear solution, (pH=6) is cooled and stirred while additional ice and water is added to cause the solution to become faintly cloudy. The precipitate is collected and recrystallized from aqueous methanol, to yield the 5-(m-fluorobenzylamino)-pyridine-2-carboxylic acid methyl ester melting at 89°-92°.

Workup

  1. temperaturethe mixture is warmed to 35° for 10-15 minutes
  2. temperatureIt is cooled
  3. distillationone-half of the methanol is distilled off
  4. concentrationthe cold concentrate
  5. temperatureThe clear solution, (pH=6) is cooled
  6. stirringstirred while additional ice and water
  7. additionis added
  8. customThe precipitate is collected
  9. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-a1bf5ee935d442e99a4871e5955d9218
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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