Lithium Hydroxide → 2,6-bis(3-cyanophenoxy)-N-methylpyridine-4-carboxamide

HRID 1700184Notes

Reaction equation

HRID 1700184 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[O:6][C:7]1[CH:12]=[C:11]([C:13](OCC)=[O:14])[CH:10]=[C:9]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=2)[N:8]=1)#[N:2].[OH-].[Li+].S(Cl)(Cl)=O.Cl.[CH3:37][NH2:38].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[O:6][C:7]1[CH:12]=[C:11]([C:13]([NH:38][CH3:37])=[O:14])[CH:10]=[C:9]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=2)[N:8]=1)#[N:2]

Participants

7

Reactant 5

HCID 3939Lithium HydroxideHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 6364545Methylamine hydrochlorideHCID 10833960HCID 10833960, compound

Product 1

HCID 104993832,6-bis(3-cyanophenoxy)-N-methylpyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To 2,6-bis(3-cyanophenoxy)pyridine-4-carboxylic acid, ethyl ester (1.6 g, 4.0 mmol) in tetrahydrofuran/water (50 mL, 1/1) was added lithium hydroxide (0.85 g, 20 mmol). After stirring for 1.5 hours the reaction was partitioned with 1 M HCl and ethyl acetate. The organic layer was separated, dried (MgSO4), and the solvent was removed in vacuo. The residue was dissolved in methylene chloride (50 mL) and thionyl chloride (2.4 g, 20 mmol) was added. After stirring for 2 hours the solvent was removed in vacuo. The residue was dissolved in methylene chloride/water (30/10 mL) and methylamine hydrochloride (0.090 g, 1.3 mmol) and potassium carbonate (0.46 g, 3.3 mmol) were added. The organic layer was separated, washed with brine, dried (MgSO4), and the solvent removed in vacuo to give 2,6-bis(3-cyanophenoxy)-N-methylpyridine-4-carboxamide; NMR (CDCl3) 7.5 (m,4), 7.3 (m,4), 7.0 (s,2), 6.25 (br s,1), 3.1 (d,3) ppm.

Workup

  1. customwas partitioned with 1 M HCl and ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in methylene chloride (50 mL)
  6. stirringAfter stirring for 2 hours the solvent
  7. customwas removed in vacuo
  8. dissolutionThe residue was dissolved in methylene chloride/water (30/10 mL)
  9. customThe organic layer was separated
  10. washwashed with brine
  11. dry with materialdried (MgSO4)
  12. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0b03428b851249029a5cac161c9223f8
Source dataset
uspto-grants-2002_02
Patent number
US06350746B1

Reaction notes

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