Hydrochloric Acid → HCID 12640162, compound

HRID 1680454Notes

Reaction equation

HRID 1680454 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:16])=[O:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.Cl.[CH3:20]O>>[CH3:20][O:15][C:14]([C:11]1[CH:10]=[CH:9][C:8]([NH:7][CH2:6][C:5]2[CH:17]=[CH:18][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:13][N:12]=1)=[O:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 126401915-{[(4-Fluorophenyl)methyl]amino}pyridine-2-carboxylic acid

Product 1

HCID 12640162HCID 12640162, compound

Procedure

50 g of 5-(p-fluorobenzylamino)-pyridine-2-carboxylic acid are suspended in 700 ml of methanol and the solution saturated with gaseous hydrogen chloride. The saturated solution is refluxed for 31/2 hours and most of the methanol is removed under reduced pressure. The concentrate is poured into ice water and the mixture neutralized with sodium bicarbonate. It is extracted with ethyl acetate-diethyl ether (1:1), the organic phase washed with water, dried and evaporated. The residue is crystallized from ethyl acetate-diethyl ether (1:5), to yield the 5-(p-fluorobenzylamino)-pyridine-2-carboxylic acid methyl ester melting at 107°-108.5°.

Workup

  1. temperatureThe saturated solution is refluxed for 31/2 hours
  2. custommost of the methanol is removed under reduced pressure
  3. additionThe concentrate is poured into ice water
  4. extractionIt is extracted with ethyl acetate-diethyl ether (1:1)
  5. washthe organic phase washed with water
  6. customdried
  7. customevaporated
  8. customThe residue is crystallized from ethyl acetate-diethyl ether (1:5)

Sources & evidence

ORD record
ord-aef3c01685ac4bf7a1cce40a6f4323fc
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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