Water → (2-Amino-6-chloro-pyridin-3-yl)-(2-methoxy-phenyl)-methanone

HRID 30101Notes

Reaction equation

HRID 30101 reaction equation
Cl[C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:18])[N:3]=1.[OH-].[NH4+:20].O.C(OCC)(=O)C>O1CCOCC1>[NH2:20][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:18])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 59789365(2,6-Dichloro-pyridin-3-yl)-(2-methoxy-phenyl)-methanone

Product 1

HCID 58590832(2-Amino-6-chloro-pyridin-3-yl)-(2-methoxy-phenyl)-methanoneYield 50.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A solution of (2,6-Dichloro-pyridin-3-yl)-(2-methoxy-phenyl)-methanone (50.3 mg, 0.178 mmol, Example 4) in 1,4-dioxane (2 mL) was treated with concentrated ammonium hydroxide (0.24 mL, 29.4%) and heated to 150° C. in the microwave for 3 hrs. The resulting mixture was treated with water and ethyl acetate, washed with saturated sodium chloride, dried over sodium sulfate and evaporated in vacuo. The residue was purified on silica gel with hexanes/ethyl acetate to give (2-Amino-6-chloro-pyridin-3-yl)-(2-methoxy-phenyl)-methanone as a off-white solid (23.7 mg, 50.7% yield). HRMS, observed: 262.0502, Calcd for M+: 262.0509.

Workup

  1. washwashed with saturated sodium chloride
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified on silica gel with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-dfd39e021ff94f919fcf4e5b0d9273fa
Source dataset
uspto-grants-2008_09
Patent number
US07423051B2

Reaction notes

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