HCID 22148752, compound → HCID 66996762, compound

HRID 1803844Notes

Reaction equation

HRID 1803844 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([F:20])[CH:19]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]([N+:14]([O-])=O)=[C:10]([CH:13]=1)[C:11]#[N:12]>O1CCOCC1.[Pd]>[NH2:14][C:9]1[CH:8]=[CH:7][C:6]([O:5][C:4]2[CH:17]=[C:18]([F:20])[CH:19]=[C:2]([F:1])[CH:3]=2)=[CH:13][C:10]=1[C:11]#[N:12]

Participants

4

Reactant 1

HCID 22148752HCID 22148752, compound

Product 1

HCID 66996762HCID 66996762, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

5-(3,5-Difluoro-phenoxy)-2-nitro-benzonitrile (7.65 g, 27.7 mmol) in dioxane (80 mL) was treated with 10% Pd/C (765 mg) and hydrogenated at 45 psi. After 6 hours the reaction was filtered through a celite funnel and washed with MeOH. The volatiles were evaporated. After purification over silica gel (eluent: hexane:EtOAc 7:3), 4.82 g of title compound were obtained as a pale yellow solid in 71% yield.

Workup

  1. filtrationAfter 6 hours the reaction was filtered through a celite funnel
  2. washwashed with MeOH
  3. customThe volatiles were evaporated
  4. customAfter purification over silica gel (eluent: hexane:EtOAc 7:3)

Sources & evidence

ORD record
ord-4e17f9ddd412454186522733ed46e42b
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

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