Ammonium Chloride → 1H-Pyrido[2,3-d]pyrimidine-2,4-dione

HRID 1784395Notes

Reaction equation

HRID 1784395 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[Cl-].[NH4+].[O-:13][C:14]#[N:15].[K+]>O>[NH:1]1[C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4](=[O:6])[NH:15][C:14]1=[O:13]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 729302-Aminonicotinic acidHCID 11378442Potassium cyanate

Product 1

HCID 2702601H-Pyrido[2,3-d]pyrimidine-2,4-dioneYield 99.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
200 °C

Procedure

A slurry of 2-aminonicotinic acid (10 g, 72.5 mmol), ammonium chloride (39 g, 725 mmol) and potassium cyanate (30 g, 362 mmol) in water (80 ml) was heated to 80° C. and maintained at this temperature with stirring for 30 minutes before being heated to 200° C. The mixture was stirred for 2 hours at this elevated temperature and then left to cool. Water (200 ml) was then added and the resultant mixture filtered. The solid was washed with hot water (100 ml) and then with cold water (2×100 ml) to give a yellow solid which corresponded to the title compound (11.79 g, 99%) in suitably clean form to be used without any further purification. m/z (LC-MSW, ESP):164 [M+H]+, R/T=2.11 mins.

Workup

  1. temperaturemaintained at this temperature
  2. stirringThe mixture was stirred for 2 hours at this elevated temperature
  3. waitleft
  4. temperatureto cool
  5. filtrationthe resultant mixture filtered
  6. washThe solid was washed with hot water (100 ml)
  7. customwith cold water (2×100 ml) to give a yellow solid which

Sources & evidence

ORD record
ord-56bb0cc15b044135b014d59f604e9693
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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