3-Cyanopyridine → HCID 18638691, compound

HRID 2073658Notes

Reaction equation

HRID 2073658 reaction equation
[CH:1]1[CH:6]=[N:5][CH:4]=[C:3]([C:7]#[N:8])[CH:2]=1.N[C@@H:10]([C:15]([OH:17])=[O:16])[C:11]([SH:14])([CH3:13])[CH3:12].C(=O)([O-])[O-:19].[K+].[K+].[ClH:24]>CO.O>[ClH:24].[C:7]([NH:8][C@@H:10]([C:15]([OH:17])=[O:16])[C:11]([SH:14])([CH3:13])[CH3:12])(=[O:19])[C:3]1[CH:2]=[CH:1][CH:6]=[N:5][CH:4]=1

Participants

7

Reactant 4

HCID 793-CyanopyridineHCID 313Hydrochloric AcidHCID 5852PenicillamineHCID 11430Potassium Carbonate

Product 1

HCID 18638691HCID 18638691, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

20.8 g (0.2 mole) nicotinic acid nitrile, 29.8 g (0.2 mole) D-penicillamine and 13.8 g (0.1 mole) potassium carbonate were heated in 350 ml methanol and 150 ml water for 6 hours at the boiling point. The mixture was acidified with concentrated hydrochloric acid to pH 4 and heated 45 minutes at the boiling point. After the mixture cooled off, 36.5 g (63% of theory) of the product precipitated as hydrochloride with a melting point of 164° C. [α]25D =+4.0° (c=2 in 1N NaOH)

Workup

  1. temperatureheated 45 minutes at the boiling point
  2. temperatureAfter the mixture cooled off
  3. custom36.5 g (63% of theory) of the product precipitated as hydrochloride with a melting point of 164° C. [α]25D =+4.0° (c=2 in 1N NaOH)

Sources & evidence

ORD record
ord-67f216b40b3847a1a48e3c37ff287052
Source dataset
uspto-grants-1990_04
Patent number
US04918223

Reaction notes

Loading…