2-(6-(Benzyloxy)-3-nitropyridin-2-yl)acetonitrile → HCID 58386519, compound

HRID 74612Notes

Reaction equation

HRID 74612 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([CH2:15][C:16]#[N:17])[C:12]([N+:18]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Ni].CCO.C(O)(=O)C>[NH2:18][C:12]1[C:13]([CH2:15][C:16]#[N:17])=[N:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 2

HCID 146572592-(6-(Benzyloxy)-3-nitropyridin-2-yl)acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 58386519HCID 58386519, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

11 g (40 mmol) (6-benzyloxy-3-nitro-pyridin-2-yl)-acetonitrile and 1.7 g Raney nickel (washed with abs. EtOH) in 120 mL EtOH and 50 mL acetic acid were hydrogenated at RT in a hydrogen atmosphere of 3 bar. The catalyst was filtered off and the filtrate was evaporated down. The residue was combined with 30 mL water and adjusted to pH=10 with solid sodium carbonate. The aqueous phase was extracted several times with EtOAc. The combined organic phases were dried on magnesium sulphate, filtered and evaporated down. The residue was purified by flash chromatography. The product-containing fractions were combined and evaporated down.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated down
  3. extractionThe aqueous phase was extracted several times with EtOAc
  4. customThe combined organic phases were dried on magnesium sulphate
  5. filtrationfiltered
  6. customevaporated down
  7. customThe residue was purified by flash chromatography
  8. customevaporated down

Sources & evidence

ORD record
ord-63bed0b2748b46bf8273e7ef027584f4
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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