Methyl 5-chloro-2-[(5-nitropyridin-2-yl)oxy]benzoate → Methyl 2-[(5-aminopyridin-2-yl)oxy]-5-chlorobenzoate

HRID 1293264Notes

Reaction equation

HRID 1293264 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][N:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]>[Pd].C(OCC)(=O)C>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])=[N:14][CH:15]=1

Participants

4

Reactant 1

HCID 69420575Methyl 5-chloro-2-[(5-nitropyridin-2-yl)oxy]benzoate

Product 1

HCID 69415937Methyl 2-[(5-aminopyridin-2-yl)oxy]-5-chlorobenzoateYield 21%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 5-chloro-2-[(5-nitropyridin-2-yl)oxy]benzoate (step 1, 1.59 g, 5.2 mmol) and 5% palladium on activated carbon (149 mg) in ethyl acetate (25 mL) was stirred at room temperature for 1 h under hydrogen atmosphere. The reaction mixture was filtered through a pad of Celite® and the filtrate was evaporated. The residue was purified by flush column chromatography on silica gel eluting with dichloromethane/methanol (50/1) to afford 301 mg (21%) of the title compound: 1H-NMR (CDCl3) δ 7.92 (1H, d, J=2.8 Hz), 7.56 (1H, d, J=2.6 Hz), 7.47 (1H, dd, J=8.7, 2.6 Hz), 7.11 (1H, dd, J=8.6, 2.8 Hz), 7.08 (1H, d, J=8.7 Hz), 6.82 (1H, d, J=8.6 Hz), 3.74 (3H, s), 3.49 (2H, br.s).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. customthe filtrate was evaporated
  3. customThe residue was purified
  4. customby flush column chromatography on silica gel eluting with dichloromethane/methanol (50/1)

Sources & evidence

ORD record
ord-370896fd1a8a49829509f46e141868ed
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

Loading…