Hydrochloric Acid → HCID 131720314, compound

HRID 2293438Notes

Reaction equation

HRID 2293438 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:11]([OH:13])=[O:12])=[O:4].[ClH:14]>CO>[ClH:14].[CH3:1][O:2][C:3]([C@H:5]1[C@@H:10]([C:11]([OH:13])=[O:12])[CH2:9][CH2:8][NH:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 8205523-methoxycarbonylpyridine-4-carboxylic acid

Product 1

HCID 131720314HCID 131720314, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridine-3,4-dicarboxylic acid 3-methyl ester (5.00 g, 27.6 mmol), prepared by the method of J. C. S. Perkin I, 1981, 3012, in methanol (50 ml) was treated with excess ethereal hydrogen chloride and the solution evaporated to dryness. The resulting salt in methanol (100 ml) was hydrogenated over platinum oxide (500 mg) at 50 p.s.i. and ambient temperature until uptake ceased (24 h). The catalyst was removed by filtration through Hyflo and the filtrate evaporated to give the title compound (6.17 g, 100%), m.p. 180°-184° (dec) δ(360 MHz, D2O ) 2.10-2.20 (2H, m, 5-CH2); 3.19-3.25 (2H, m, 3-CH, 4-CH); 3.27-3.32 (1H, m, 6-CH ax); 3.34-3.39 (1H, m, 6-CH eq); 3.51 (1H,dd, J13 Hz and 4 Hz, 2-CH eq); 3.60 91H, dd, J 7.5 Hz and 13 Hz, 2-CH ax).

Workup

  1. customthe solution evaporated to dryness
  2. customambient temperature
  3. custom(24 h)
  4. customThe catalyst was removed by filtration through Hyflo
  5. customthe filtrate evaporated

Sources & evidence

ORD record
ord-33ccdec2fd544b05aef06fd26e4eeb72
Source dataset
uspto-grants-1997_11
Patent number
US05686463

Reaction notes

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