4-Nitrobenzaldehyde → HCID 178526539, compound

HRID 854073Notes

Reaction equation

HRID 854073 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

HCID 5414-NitrobenzaldehydeHCID 34801515-Nitropyridine-2,3-diamine

Product 1

HCID 178526539HCID 178526539, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

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)

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. filtrationthe resulting orange solid collected by filtration
  3. washThe filter cake was washed with ether and air
  4. customdried

Sources & evidence

ORD record
ord-d4cb2141e51d46b5a89615ed0aeba23f
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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