Water → HCID 67252633, compound

HRID 2042065Notes

Reaction equation

HRID 2042065 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([N+:17]([O-])=O)[CH:16]=2)[C:12]#[N:13])=[CH:4][CH:3]=1.O.C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.[Fe]>[NH2:17][C:15]1[CH:14]=[C:11]([CH:10]=[C:9]([O:8][C:5]2[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:16]=1)[C:12]#[N:13]

Participants

6

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 67252915HCID 67252915, compound

Product 1

HCID 67252633HCID 67252633, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-(6-methylpyridin-3-yloxy)-5-nitrobenzonitrile (3 g, 0.012 mol) and iron powder in acetic acid (200 mL) was stirred at RT for 6 h. H2O was added and the mixture was adjusted to pH 7 with saturated Na2CO3 solution. The aqueous layer was extracted with EtOAc, and the combined organics were washed with brine, dried (MgSO4), concentrated in vacuo and purified by silica gel chromatography to afford 3-amino-5-(6-methylpyridin-3-yloxy)benzonitrile (2 g, 76% yield). 1H NMR (400 MHz, DMSO) δ 8.25 (s, 1H), 7.42 (d, J=10 Hz, 1H), 7.30 (d, J=8.4 Hz, 1H), 6.62 (s, 1H), 6.51 (s, 1H), 6.38 (s, 1H), 5.78 (s, 2H), 2.49 (s, 3H); MS (ESI) m/z: 226.2 [M+H]+.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washthe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-6b9062cb1c47404d866adea925a49ddc
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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