HCID 57742094, compound → HCID 57742044, compound

HRID 1879999Notes

Reaction equation

HRID 1879999 reaction equation
[CH3:1][C:2]([CH3:18])([CH2:7][O:8][C:9]1[C:10]([N+:15]([O-])=O)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:3]([O:5][CH3:6])=[O:4]>CO.[Pd]>[CH3:1][C:2]([CH3:18])([CH2:7][O:8][C:9]1[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 1

HCID 57742094HCID 57742094, compound

Product 1

HCID 57742044HCID 57742044, compoundYield 611.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of methyl 2,2-dimethyl-3-(2-nitropyridin-3-yloxy)propanoate (9.1 g, 6 mmol) and Pd/C (800 mg) in methanol (500 mL) was stirred at rt overnight under hydrogen. The cooled mixture was filtered through celite, washed with methanol and evaporated in vacuo to afford the title compound (8.23 g, 100%). 1H NMR (300 MHz, DMSO-d6) δ 7.51 (d, J=1.3 Hz, 1H), 7.03 (d, J=1.3 Hz, 1H), 6.47 (m, 1H), 5.47 (s, 2H), 3.94 (s, 2H), 3.62 (s, 3H), 1.17 (s, 6H)

Workup

  1. filtrationThe cooled mixture was filtered through celite
  2. washwashed with methanol
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-3128ddd6c0e147af894603f2e3eaca4d
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

Loading…