Methanol → HCID 12640161, compound

HRID 1680434Notes

Reaction equation

HRID 1680434 reaction equation
[BH4-].[Na+].CO.[CH3:5][O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([N:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[CH:11][N:10]=1)=[O:8]>CN(C)C=O>[CH3:5][O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[CH:11][N:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 12640216HCID 12640216, compound

Product 1

HCID 12640161HCID 12640161, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the stirred mixture of 8 g of sodium borohydride and 350 ml of methanol, cooled to -2°, the solution of 20 g of 5-(m-chlorobenzylideneamino)-pyridine-2-carboxylic acid methyl ester in 60 ml of dimethylformamide sufficiently warm for dissolution is added all at once and the container of the latter is washed with 15 ml dimethylformamide and 20 ml methanol containing 0.5 g of sodium borohydride. The mixture warms to about 20°, is cooled to 0° for 40 minutes and stirred at 25° for 15 minutes. It is cooled again to 0° and 9 ml of 12 N hydrochloric acid, 2 ml of acetic acid and 200 ml of ice water are added in this order. The resulting solution is diluted with crushed ice to about 1,000 ml, extracted with ethyl acetate and diethyl ether, the extract dried and evaporated. The residue is first recrystallized from diethyl ether/hexane and then from ethyl acetate/diethyl ether, to yield the 5-(m-chlorobenzylamino)-pyridine-2-carboxylic acid methyl ester of the formula ##STR9## melting at 111°-113°.

Workup

  1. temperaturecooled to -2°
  2. additionis added all at once and the container of the latter
  3. washis washed with 15 ml dimethylformamide and 20 ml methanol containing 0.5 g of sodium borohydride
  4. customwarms to about 20°
  5. temperatureis cooled to 0° for 40 minutes
  6. temperatureIt is cooled again to 0°
  7. addition9 ml of 12 N hydrochloric acid, 2 ml of acetic acid and 200 ml of ice water are added in this order
  8. additionThe resulting solution is diluted with crushed ice to about 1,000 ml
  9. extractionextracted with ethyl acetate and diethyl ether
  10. customthe extract dried
  11. customevaporated
  12. customThe residue is first recrystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-f4265863801c486f84297effe0ca0279
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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