Methylamine → HCID 54151562, compound

HRID 615137Notes

Reaction equation

HRID 615137 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:17]2[CH:18]=[N+:19]([O-:23])[CH:20]=[CH:21][CH:22]=2)[C:8]2[C:15](=[O:16])[O:14][CH2:13][C:9]=2[NH:10][C:11]=1[CH3:12])=[O:5])[CH3:2].[CH3:24][NH2:25]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:17]2[CH:18]=[N+:19]([O-:23])[CH:20]=[CH:21][CH:22]=2)[C:8]([C:15]([NH:25][CH3:24])=[O:16])=[C:9]([CH2:13][OH:14])[NH:10][C:11]=1[CH3:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 70489174HCID 70489174, compound

Product 1

HCID 54151562HCID 54151562, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10.0 g of 2-methyl-4-(1-oxido-3-pyridyl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylic acid ethyl ester and 100 ml of a 33% solution of methylamine in ethanol is heated at 90° in a sealed tube for 16 hours. The reaction mixture is concentrated to dryness by evaporation under reduced pressure and the residue is partitioned between methylene chloride and a 2N aqueous sodium carbonate solution. The organic phase is removed, washed with water, dried and concentrated by evaporation under reduced pressure. The residue is chromatographed over silica gel and eluted with ethyl acetate. The uniform fractions ascertained by means of a thin layer chromatograph are concentrated to dryness by evaporation under reduced pressure and the residue is recrystallised from a mixture of isopropanol and petroleum ether to yield 6-hydroxymethyl-2-methyl-5-methylaminocarbonyl-4-(1-oxido-3-pyridyl)-1,4-dihydropyridine-3-carboxylic acid ethyl ester melting at 197°.

Workup

  1. temperatureis heated at 90° in a sealed tube for 16 hours
  2. concentrationThe reaction mixture is concentrated to dryness by evaporation under reduced pressure
  3. customthe residue is partitioned between methylene chloride
  4. customThe organic phase is removed
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe residue is chromatographed over silica gel
  9. washeluted with ethyl acetate
  10. concentrationare concentrated to dryness by evaporation under reduced pressure
  11. customthe residue is recrystallised from a mixture of isopropanol and petroleum ether

Sources & evidence

ORD record
ord-c150d0b4f8d24c559ebf15c293889faa
Source dataset
uspto-grants-1985_02
Patent number
US04497808

Reaction notes

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