4-Nitrobenzaldehyde → HCID 178526539, compound
Reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)([O-:14])=[O:13]>[N+](C1C=CC=CC=1)([O-])=O>[N+:9]([C:5]1[CH:4]=[N:3][C:2]2[NH:1][C:19]([C:18]3[CH:21]=[CH:22][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=3)=[N:8][C:7]=2[CH:6]=1)([O-:11])=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 175 °C
Procedure
To a stirred solution of 2,3-diamino-5-nitropyridine (3) (400 mg, 2.6 mmol) in nitrobenzene (50 mL) was added 4-nitrobenzaldehyde (393 mg, 2.6 mmol) and the mixture heated at 175° C. for 24 h. The solvent was removed by distillation under reduced pressure and the resulting orange solid collected by filtration using CH3CN. The filter cake was washed with ether and air dried to give 4 as an orange solid (0.614 g, 2.1 mmol, 83%) that was used as is without further purification. 1H NMR (500 MHz, DMSO-d6) δ14.58 (br s, 1H), 9.28 (apparent d, 1H), 8.88 (br s, 1H), 8.51 (d, J=8.39 Hz, 2H), 8.45 (d, J=8.28 Hz, 2H). EIMS M−1 284.3. Rf=0.55 (silica, 19:1 DCM/MeOH)