HCID 66818891, compound → HCID 66818531, compound

HRID 1024671Notes

Reaction equation

HRID 1024671 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[C:10]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)[N:9]=2)=[CH:5][CH:4]=1)#[N:2]>CO.C(OCC)(=O)C.[Pd].[C]>[NH2:14][C:13]1[C:8]([O:7][C:6]2[CH:26]=[CH:27][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[N:9][C:10]([O:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 66818891HCID 66818891, compound

Product 1

HCID 66818531HCID 66818531, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

10% Pd/carbon (0.24 g) was added under hydrogen atmosphere (balloon pressure) to a stirred solution of 2,6-Bis(4-Cyano phenoxy)-3-nitro pyridine (1.20 g, 3.35 mmol) in 20 ml of methanol:ethyl acetate (1:1) at ambient temperature and the reaction mixture was stirred for 1 h. The reaction mixture was filtered through celite, washed with 20 ml of ethyl acetate and concentrated under reduced pressure. Water was added to the residual mixture and it was extracted with ethyl acetate. Ethyl acetate layer was washed with water followed by brine. The organic layer was dried over sodium sulphate to afford 0.95 g of the title product which was used for the next step without further purification. 1H NMR (DMSO-d6): δ 5.32 (2H, brs), 6.82 (1H, d), 7.15 (1H, d), 7.22 (2H, d), 7.34 (2H, d), 7.80 (4H, m).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with 20 ml of ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added to the residual mixture and it
  5. extractionwas extracted with ethyl acetate
  6. washEthyl acetate layer was washed with water
  7. dry with materialThe organic layer was dried over sodium sulphate

Sources & evidence

ORD record
ord-6b28076350b44b3babd876a1f288e1ac
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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