Acetic Acid → HCID 12907794, compound

HRID 1680446Notes

Reaction equation

HRID 1680446 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][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)=[CH:7][N:6]=1)=[O:4].[BH4-].[Na+].C(O)(=O)C.Cl>CN(C)C=O.CO.O>[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][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)=[CH:7][N:6]=1)=[O:4]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 54019484HCID 54019484, compound

Product 1

HCID 12907794HCID 12907794, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The solution of 13.7 g of 5-(3,4-dichlorobenzylideneamino)-pyridine-2-carboxylic acid methyl ester in 35 ml of hot dimethylformamide is added all at once to the solution of 3.25 g of sodium borohydride in 150 ml of methanol while stirring at -20°. The mixture warms to 10° and the temperature is lowered by application of a bath to 0°. After one hour the reaction mixture is warmed to 35° for 10 minutes, cooled again to 0° and 1.5 ml of acetic acid and the solution of 6 ml 12 N hydrochloric acid in 45 ml of ice water is added. A solid separates, more ice and water are added to complete crystallization. The solid is collected, washed with cold water and recrystallized from methanol, to yield the 5-(3,4-dichlorobenzylamino)-pyridine-2-carboxylic acid methyl ester melting at 158°-161°.

Workup

  1. customwarms to 10°
  2. customthe temperature is lowered by application of a bath to 0°
  3. temperatureAfter one hour the reaction mixture is warmed to 35° for 10 minutes
  4. temperaturecooled again to 0°
  5. customThe solid is collected
  6. washwashed with cold water
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5cdcefb9ebb345fcac2800de533dd597
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

Loading…