HCID 18522056, compound → HCID 18522062, compound

HRID 413750Notes

Reaction equation

HRID 413750 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-])=O)[C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([Cl:19])[CH:12]=1)([O-])=O>[Pd].C(O)C>[ClH:19].[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26])[C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([Cl:19])[CH:12]=1

Participants

4

Reactant 1

HCID 18522056HCID 18522056, compound

Product 1

HCID 18522062HCID 18522062, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N,N-Bis(2-nitrophenyl)-3-chloro-4-cyanoaniline, palladium on carbon (0.70 g, 5%), ethanol (100 ml) was stirred under hydrogen until 2.5 l was consumed. The reaction mixture was filtered through a celite pad, hydrogen chloride in methanol (4M, 30 ml) was added and the solvent was removed by evaporation. The residue was triturated with ethyl acetate to leave the crystalline product. Yield 3.8 g, 53%. M.p. 184-187° C.

Workup

  1. customwas consumed
  2. filtrationThe reaction mixture was filtered through a celite pad, hydrogen chloride in methanol (4M, 30 ml)
  3. additionwas added
  4. customthe solvent was removed by evaporation
  5. customThe residue was triturated with ethyl acetate
  6. customto leave the crystalline product

Sources & evidence

ORD record
ord-73b55ba36bdc4a8f86acc8f2262e8729
Source dataset
uspto-grants-2003_05
Patent number
US06569880B2

Reaction notes

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