3-Chloro-5-(3-nitrophenoxy)pyridine → 3-(5-Chloropyridin-3-yloxy)benzenamine

HRID 1696447Notes

Reaction equation

HRID 1696447 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=2)[CH:7]=1>CCOC(C)=O.O=[Pt]=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=2)[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 1

HCID 229938583-Chloro-5-(3-nitrophenoxy)pyridine

Product 1

HCID 229938803-(5-Chloropyridin-3-yloxy)benzenamineYield 93.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-chloro-5-(3-nitrophenoxy)pyridine (0.2 g, 0.8 mmol) in EtOAc (10 mL) was added PtO2 (0.02 g) and the mixture was stirred for 4 h under H2 (1 atm). It was then filtered through a Celite® pad and washed with EtOAc (2×5 mL). The combined organic extracts were concentrated to afford 3-(5-chloropyridin-3-yloxy)benzenamine (0.165 g, 93% yield) which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.39 (d, J=2.0 Hz, 1H), 8.31 (d, J=2.8 Hz, 1H), 7.54-7.53 (m, 1H), 7.05 (t, J=8.0 Hz, 1H), 6.42-6.39 (m, 1H), 6.25-6.19 (m, 2H), 5.33 (brs, 2H); MS (ESI) m/z: 221.0 (M+H+).

Workup

  1. filtrationIt was then filtered through a Celite® pad
  2. washwashed with EtOAc (2×5 mL)
  3. concentrationThe combined organic extracts were concentrated

Sources & evidence

ORD record
ord-4e5efa12a62e46c4bdba7f7fa1917527
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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