2-Nitro-6-cyclopropylbenzonitrile → 2-Amino-6-cyclopropylbenzonitrile

HRID 631878Notes

Reaction equation

HRID 631878 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]2[CH2:14][CH2:13]2)[C:5]=1[C:6]#[N:7])([O-])=O.[H][H]>[Pd].C(Cl)Cl.C(O)C>[NH2:1][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]2[CH2:13][CH2:14]2)[C:5]=1[C:6]#[N:7]

Participants

6

Reactant 2

HCID 682964052-Nitro-6-cyclopropylbenzonitrile2×HCID 178418361HCID 178418361, compound

Product 1

HCID 667472522-Amino-6-cyclopropylbenzonitrileYield 39%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A slurry of palladium on carbon (10%; 0.025 g) in DCM (5 mL) was added to a solution of 2-nitro-6-cyclopropylbenzonitrile (Intermediate 11, 0.25 g) in ethanol (15 mL) under nitrogen. The nitrogen atmosphere was exchanged for hydrogen and the mixture was stirred for 48 hours. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by flash chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane. The fractions containing the desired product were combined and evaporated to give the title compound as a colorless oil (0.082 g).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified by flash chromatography on silica
  4. washeluting with a mixture of ethyl acetate and cyclohexane
  5. additionThe fractions containing the desired product
  6. customevaporated

Sources & evidence

ORD record
ord-4b2479d234614e0399fa74034506ed8b
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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