2-(2,2-Dimethyl-2,3-dihydrobenzofuran-7-yloxy)-3-nitropyridine → 2-(2,2-Dimethyl-2,3-Dihydrobenzofuran-7-yloxy)pyridin-3-Amine

HRID 555409Notes

Reaction equation

HRID 555409 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][C:12]3[C:17]([N+:18]([O-])=O)=[CH:16][CH:15]=[CH:14][N:13]=3)[C:4]=2[O:3]1>CO.C(OCC)(=O)C.[Pd]>[CH3:1][C:2]1([CH3:21])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][C:12]3[C:17]([NH2:18])=[CH:16][CH:15]=[CH:14][N:13]=3)[C:4]=2[O:3]1

Participants

5

Reactant 1

HCID 39410562-(2,2-Dimethyl-2,3-dihydrobenzofuran-7-yloxy)-3-nitropyridine

Product 1

HCID 167946592-(2,2-Dimethyl-2,3-Dihydrobenzofuran-7-yloxy)pyridin-3-AmineYield 97%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

134a (3.27 g, 11.4 mmol) was dissolved in a 1:1 mixture of methanol and ethyl acetate (80 mL). Palladium on charcoal (10%, 1.2 g, 1.1 mmol) was added, and the mixture was stirred 1 h under hydrogen atmosphere (40 psi). The reaction mixture was filtered over Celite® and concentrated to afford 2.78 g (97% yield, 100% pure) of 134b as an off-white solid. [M+H]+=257.17; in NMR (500 MHz, deuterochloroform) δ ppm 7.53 (d, 1H, J=5.0 Hz), 6.97 (d, 2H, J=10.0 Hz), 6.95 (d, 1H, J=5.0 Hz), 6.80 (m, 2H), 3.97 (br, 2H), 3.05 (s, 2H), 1.44 (s, 6H); 13C (125 MHz, deuterochloroform) δ (ppm), 151.60, 150.18, 137.70, 135.60, 131.52, 129.47, 121.77, 121.30, 120.96, 120.27, 119.02, 87.80, 43.19, 28.08.

Workup

  1. filtrationThe reaction mixture was filtered over Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-37cc7bd4dc1845f2a69e43bf230522f7
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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