Malonamide → HCID 178513675, compound

HRID 1020806Notes

Reaction equation

HRID 1020806 reaction equation
CN1[CH:7]=[CH:6][C:5](=[O:8])N(C)C1=O.[C:11]([NH2:17])(=[O:16])[CH2:12][C:13]([NH2:15])=[O:14].[O-]CC.[Na+]>CCO>[OH:14][C:13]1[N:15]=[C:5]([OH:8])[CH:6]=[CH:7][C:12]=1[C:11]([NH2:17])=[O:16]

Participants

5

Reactant 3

HCID 7911MalonamideHCID 701221,3-DimethyluracilHCID 2723922Sodium ethoxide

Product 1

HCID 178513675HCID 178513675, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of compound 1,3-dimethylpyrimidine-2,4(1H,3H)-dione (14 g, 0.1 mol), malonamide (45 g, 0.44 mol) and sodium ethoxide (34 g, 0.4 mol) in EtOH (500 mL) was refluxed for 20 mins. The mixture was cooled to r.t, quenched by water and acidified with 1 M HCl to pH=1-2. The solid was filtered and the filter cake was concentrated in vacuo to afford compound 2,6-dihydroxynicotinamide. (10 g, yield: 65%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 7.90-7.88 (d, 1H), 5.66-5.64 (d, 1H).

Workup

  1. temperaturewas refluxed for 20 mins
  2. temperatureThe mixture was cooled
  3. customquenched by water
  4. filtrationThe solid was filtered
  5. concentrationthe filter cake was concentrated in vacuo

Sources & evidence

ORD record
ord-9591e8f4d4994c639c588edce3d4aefc
Source dataset
uspto-grants-2014_05
Patent number
US08716478B2

Reaction notes

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