Nitric Acid → 2-(2-Ethoxy-5-nitrophenyl)-8-n-propylpyrido[3,2-d]pyrimidin-4(3H)-one

HRID 1107307Notes

Reaction equation

HRID 1107307 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:11][C:12](=[O:23])[C:13]2[N:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][CH3:22])[C:14]=2[N:15]=1)[CH3:2].S(=O)(=O)(O)O.[N+:29]([O-])([OH:31])=[O:30]>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:29]([O-:31])=[O:30])=[CH:6][C:5]=1[C:10]1[NH:11][C:12](=[O:23])[C:13]2[N:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][CH3:22])[C:14]=2[N:15]=1)[CH3:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 1361763052-(2-Ethoxyphenyl)-8-n-propylpyrido[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 1354943292-(2-Ethoxy-5-nitrophenyl)-8-n-propylpyrido[3,2-d]pyrimidin-4(3H)-oneYield 77%

Procedure

A solution of 2-(2-ethoxyphenyl)-8-n-propylpyrido-(3,2-d]pyrimidin-4(3H)-one (Preparation 8; 0.80 g, 0.0026 mol) in a mixture of concentrated sulphuric acid (5.4 ml) and concentrated nitric acid (0.20 ml) was stirred at ambient temperature for 4.5 hours. The mixture was then poured cautiously into stirred ice/water (50 g) and the resulting mixture extracted with a methanol:dichloromethane mixture (1:9, 3×50 ml). The organic extracts were combined, dried (MgSO4) and evaporated under vacuum, and the residue crystallized from ethyl acetate:methanol to give the title compound as an off-white solid (0.71 g, 77%), m.p. 257-259° C.

Workup

  1. additionThe mixture was then poured cautiously
  2. extractionthe resulting mixture extracted with a methanol
  3. dry with materialdried (MgSO4)
  4. customevaporated under vacuum
  5. customthe residue crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ed6a5af99f1e4349876ce329e59d51cf
Source dataset
uspto-grants-2000_05
Patent number
US06060477

Reaction notes

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