Isopropylamine → 2-amino-N-isopropylnicotinamide

HRID 268334Notes

Reaction equation

HRID 268334 reaction equation
[C:1]12[C:7](=[N:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[CH:13]([NH2:16])([CH3:15])[CH3:14]>CN(C)C=O>[NH2:6][C:7]1[N:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:16][CH:13]([CH3:15])[CH3:14])=[O:4]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 109865823-Azaisatoic anhydride

Product 1

HCID 215514072-amino-N-isopropylnicotinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In addition to being useful as discussed above, acid anhydrides produced by the method of the invention are useful as intermediates for the production of pyrimidine diones which can be used as herbicides. For example, 3-azaisatoic anhydride can be dissolved in dimethylformamide and reacted with a substantially stoichiometric amount of isopropyl amine to produce 2-amino-N-isopropylnicotinamide. The reaction is conveniently conducted at a temperature of about 45°-50° until carbon dioxide evolution ceases. The 2-amino-N-isopropylnicotinamide can then be reacted with phosgene to produce 3-isopropyl pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione. This reaction can be conducted under ambient pressure in p-dioxane as a solvent, preferably in the presence of triethylamine as an HCl absorber, at a temperature in the vicinity of 100°.

Workup

  1. additionIn addition
  2. customproduced by the method of the invention

Sources & evidence

ORD record
ord-298cd15164f542aeb4d7306af2641b60
Source dataset
uspto-grants-1976_03
Patent number
US03947442

Reaction notes

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