Ammonium Chloride → HCID 66820986, compound

HRID 1024707Notes

Reaction equation

HRID 1024707 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=3)[CH:11]=[CH:10][C:9]=2[N+:23]([O-])=O)=[CH:5][CH:4]=1)#[N:2].[Cl-].[NH4+]>CO.[Zn]>[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=3)[CH:11]=[CH:10][C:9]=2[NH2:23])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 66821097HCID 66821097, compound

Product 1

HCID 66820986HCID 66820986, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Zinc dust, 0.4 g (5.3 mmol) was added portionwise to a reaction flask containing a stirred mixture (10 min) of 1,5-bis-(4-cyano-phenoxy)-2-nitrobenzene 1.5 g (4.2 mmol) and 0.085 g (0.08 mmol) of ammonium chloride dissolved in 25 ml of methanol. The reaction mixture was allowed to stir for 1 h at RT. Reaction mixture was filtered through celite and the filtrate was concentrated to afford a brown viscous residue which was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate and concentrated to afford an oily residue, which was purified by column chromatography using chloroform-ethyl acetate (10:1) to afford 1.3 g of the required product. 1H NMR (DMSO-d6): δ 5.10 (2H, brs), 6.85 (3H, m), 7.06 (4H, m), 7.80 (4H, m).

Workup

  1. customReaction mixture
  2. filtrationwas filtered through celite
  3. concentrationthe filtrate was concentrated
  4. customto afford a brown viscous residue which
  5. customwas partitioned between ethyl acetate and water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto afford an oily residue, which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9e888f3e387e41b8be0e9f324f5708fc
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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