Ethyl 2-formyl-3-(3-methoxyphenyl)propionate → 2-Nitroamino-5-(3-methoxybenzyl)-4-pyrimidone

HRID 1248314Notes

Reaction equation

HRID 1248314 reaction equation
[CH:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[C:4](OCC)=O)=[O:2].C[O-].[Na+].[N+:21]([NH:24][C:25]([NH2:27])=[NH:26])([O-:23])=[O:22]>CO>[N+:21]([NH:24][C:25]1[NH:27][C:1](=[O:2])[C:3]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[CH:4][N:26]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 10823703Ethyl 2-formyl-3-(3-methoxyphenyl)propionateHCID 10942334Sodium MethoxideHCID 86287517Nitroguanidine

Product 1

HCID 202792742-Nitroamino-5-(3-methoxybenzyl)-4-pyrimidoneYield 29.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-formyl-3-(3-methoxyphenyl)propionate (10 g) was added dropwise to a stirred and boiling mixture of sodium methoxide (from 1.15 g sodium) and nitroguanidine (25% wet, 5.5 g) in methanol (250 ml) and the mixture was heated under reflux for 20 hours and evaporated to dryness. The residue was dissolved in water (100 ml), the solution was extracted with ether and the aqueous phase was adjusted to pH 4: the solid which separated was recrystallized from ethanol to give 2-nitroamino-5-(3-methoxybenzyl)-4-pyrimidone (3.41 g, 29%), m.p 178°-9°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 hours
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in water (100 ml)
  5. extractionthe solution was extracted with ether
  6. customthe solid which separated
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-254f0dbd6a2f447685cbf565d380c568
Source dataset
uspto-grants-1985_06
Patent number
US04523015

Reaction notes

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