O-Toluidine → HCID 53269523, compound

HRID 1242165Notes

Reaction equation

HRID 1242165 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([N+]([O-])=O)[CH:11]=1>C(O)C>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[C:14]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH3:8])[CH:15]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 330974-Chloro-1,2-dinitrobenzene

Product 1

HCID 53269523HCID 53269523, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

81 ml of o-toluidine was added to absolution of 10 g of 1-chloro-3,4-dinitrobenzene in 50 ml of ethanol, and it was refluxed for 72 hours. It was concentrated by evaporation in a vacuum, the residue was taken up in ethyl acetate and 2N aqueous hydrochloric acid. The organic phase was extracted three more times with 2N aqueous hydrochloric acid, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was purified by chromatography on silica gel.

Workup

  1. temperaturewas refluxed for 72 hours
  2. concentrationIt was concentrated by evaporation in a vacuum
  3. extractionThe organic phase was extracted three more times with 2N aqueous hydrochloric acid
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-629d4147d2c44ce28ce8b452545d6b58
Source dataset
uspto-grants-2006_10
Patent number
US07115645B2

Reaction notes

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