Ammonium Carbonate → HCID 86640695, compound

HRID 2176115Notes

Reaction equation

HRID 2176115 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:11]=O)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[NH4+].[NH4+]>C(#N)C.O.[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[NH2:11])=[CH:6][N:7]=1

Participants

6

Reactant 2

HCID 517111Ammonium CarbonateHCID 86640694HCID 86640694, compound

Product 1

HCID 86640695HCID 86640695, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A 250 mL flask was charged with N-(2-(6-chloropyridin-3-yl)ethyl)-N-p-tolylnitrous amide (5.2 g, 18.9 mmol; Example 117C) and ammonium carbonate (3.62 g, 37.7 mmol; Aldrich) in acetonitrile (10 mL) and water (30 mL). The mixture was cooled in an ice bath and zinc dust (1.63 g, 24.5 mmol; Aldrich) was added very slowly over 2 hours. After stirring for an additional 1 hour, the reaction was filtered to remove the solid material. The filtrate was concentrated and extracted with ethyl acetate. The organic extracts were then purified by flash chromatography (silica gel, hexane/ethyl acetate, 2:1) to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 2.22 (s, 3H), 2.89-2.99 (m, 2H), 3.52-3.60 (m, 2H), 6.81-6.90 (m, 2H), 6.98-7.04 (m, 2H), 7.36 (d, J=8 Hz, 1H), 7.74 (dd, J=8, 3 Hz, 1H), 8.25 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 262 (M+H)+.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. filtrationthe reaction was filtered
  3. customto remove the solid material
  4. concentrationThe filtrate was concentrated
  5. extractionextracted with ethyl acetate
  6. customThe organic extracts were then purified by flash chromatography (silica gel, hexane/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-c03b1df0636f46c2a06e0ee34391a8d3
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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