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

HRID 903368Notes

Reaction equation

HRID 903368 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 recrystallised 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 recrystallised from ethanol

Sources & evidence

ORD record
ord-e1bca08bdd4743a99de86e3e0437b806
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

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