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

HRID 991476Notes

Reaction equation

HRID 991476 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 vacua. 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 vacua
  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-9bd523ae4e2b45a6b39af66ab87bbee6
Source dataset
uspto-grants-2002_10
Patent number
US06465459B2

Reaction notes

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