Pyridine → HCID 86661734, compound

HRID 1020826Notes

Reaction equation

HRID 1020826 reaction equation
[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:5]([C:6]([NH2:8])=O)=[C:4]([O:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[N:3]=1.O=P(Cl)(Cl)Cl.N1C=CC=CC=1.[OH-].[Na+]>C(#N)C>[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:5]([C:6]#[N:8])=[C:4]([O:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[N:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 86661732HCID 86661732, compound

Product 1

HCID 86661734HCID 86661734, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-chloro-2-(2-isopropoxyethoxy)-5-(trifluoromethyl)nicotinamide (0.2 g, 0.61 mmol) in acetonitrile (20 mL) was added POCl3 (0.28 g, 1.84 mmol) and pyridine (0.29 g, 3.68 mmol). After stirred at r.t for 1 hr, the mixture was diluted by 0.2 M NaOH solution, extracted by EtOAc and the organic layer was concentrated in vacuo to afford 6-chloro-2-(2-isopropoxyethoxy)-5-(trifluoromethyl)nicotinonitrile. (180 mg, 95.7%). 1H-NMR (400 MHz, CDCl3) δ (ppm) 8.14 (s, 1H), 4.64-4.61 (t, 2H), 3.83-3.81 (t, 2H), 3.72-3.66 (m, 1H), 1.19-1.17 (d, 6H).

Workup

  1. extractionextracted by EtOAc
  2. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-5630268677644cf1b07378e4939df410
Source dataset
uspto-grants-2014_05
Patent number
US08716478B2

Reaction notes

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