3-Nitrobenzaldehyde → HCID 2921732, compound

HRID 1982376Notes

Reaction equation

HRID 1982376 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[CH:3]=1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13].[C:23]([O:29][CH3:30])(=[O:28])[CH2:24][C:25]([CH3:27])=O>C(O)(=O)C>[CH3:8][N:7]1[C:2]2[NH:1][C:25]([CH3:27])=[C:24]([C:23]([O:29][CH3:30])=[O:28])[CH:18]([C:17]3[CH:20]=[CH:21][CH:22]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=3)[C:3]=2[C:4](=[O:11])[N:5]([CH3:10])[C:6]1=[O:9]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 7757Methyl acetoacetateHCID 811526-Amino-1,3-dimethyluracil

Product 1

HCID 2921732HCID 2921732, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6-amino-N,N'-dimethyluracil (3.1 g,20 mM),3-nitrobenzaldehyde (3 g,20 mM), and methyl acetoacetate (2.3 g, 1.4 ml, 20 mM) in glacial acetic acid (10 ml) was stirred under N2 at reflux for 3 hours, cooled to ambient, light yellow solid which was filtered and rinsed with acetone to give the title compound (1.04 g,13.5%),mp >230° C.

Workup

  1. temperatureat reflux for 3 hours
  2. temperaturecooled to ambient, light yellow solid which
  3. filtrationwas filtered
  4. washrinsed with acetone

Sources & evidence

ORD record
ord-15204affe4764727b228f8716ed2d003
Source dataset
uspto-grants-1986_06
Patent number
US04596805

Reaction notes

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