Hydrochloric Acid → HCID 19029066, compound

HRID 2255923Notes

Reaction equation

HRID 2255923 reaction equation
[ClH:1].[CH2:2]([N:4]([C:11]1[CH:16]=[C:15]([CH3:17])[N:14]=[C:13](OCC)[CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:3].C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH2:28]([CH2:30][NH2:31])[OH:29]>O.C(OCC)(=O)C>[ClH:1].[CH2:2]([N:4]([C:11]1[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]([NH:31][CH2:30][CH2:28][OH:29])[CH:12]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 10340Sodium CarbonateHCID 19029068HCID 19029068, compound

Product 1

HCID 19029066HCID 19029066, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(N-ethylanilino)-2-ethoxy-6-methylpyridine hydrochloride (0.584 g, 2 mM) in ethanolamine (5 ml) was heated under argon at 180° C. for 24 hours. The solution was cooled, diluted with water (50 ml), basified with aqueous sodium carbonate solution and extracted with methylene chloride (4×10 ml). The organic extracts were combined, dried (MgSO4) and evaporated to give a gum. This gum was triturated with ether to give, 4-(N-ethylanilino)-2-hydroxy-6-methylpyridine as a white solid (0.05 g) which was collected by filtration. The filtrate was evaporated and the residue was purified by flash column chromatography, eluting successively with methanol/methylene chloride (1:19 v/v), methanol/methylene chloride, (1:9 v/v/) and methanol/methylene chloride/0.88d aqueous NH4OH (20:80:1 v/v) to give a gum. This gum was dissolved in ethyl acetate and treated with etheral hydrogen chloride to give a gum which solidified on standing. The solid was washed with ether to give 4-(N-ethylanilino)-2-(2-hydroxyethylamino)-6-methylpyridine hydrochloride (0.15 g, 24% yield); m.p. 190° C.; microanalysis, found C, 62.2; H, 7.5; N, 13.7%; C16H22N3OCl requires: C, 62.4; H, 7.15; N, 13.6%; NMR: 1.1-1.2 (3H, t, CH3), 2.23(3H, s, CH3), 3.2-3.32(2H, q, CH2), 3.5-3.6(2H, t, CH2), 3.7-3.85(2H, q, CH2), 5.7(1H, s, CH), 5.9(1H, s, CH), 7.2-7.6(5H, complex, aromatic), 4.7-5.1(1H, broad, OH), 12.4(1H, NH).

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with methylene chloride (4×10 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a gum
  6. customThis gum was triturated with ether
  7. customto give
  8. filtration4-(N-ethylanilino)-2-hydroxy-6-methylpyridine as a white solid (0.05 g) which was collected by filtration
  9. customThe filtrate was evaporated
  10. customthe residue was purified by flash column chromatography
  11. washeluting successively with methanol/methylene chloride (1:19 v/v), methanol/methylene chloride, (1:9 v/v/) and methanol/methylene chloride/0.88d aqueous NH4OH (20:80:1 v/v)
  12. customto give a gum
  13. customto give a gum which
  14. washThe solid was washed with ether

Sources & evidence

ORD record
ord-156751542d3140008df6e1a5e1d02a84
Source dataset
uspto-grants-1997_08
Patent number
US05654298

Reaction notes

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