Sodium hydride → HCID 23042892, compound

HRID 2165518Notes

Reaction equation

HRID 2165518 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[NH2:17].[H-].[Na+]>CN(C)C=O>[CH:12]1[C:11]2[O:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3](=[O:2])[NH:17][C:16]=2[CH:15]=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 15057056HCID 15057056, compound

Product 1

HCID 23042892HCID 23042892, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-amino-3-pyridyloxy)benzoic acid methyl ester (7.5 g) in dimethylformamide (25 ml) was slowly added to a suspension of sodium hydride (60%) oil dispersion, 1.4 g), washed with hexanes, in dimethylformamide (5 ml). After one hr, the reaction mixture was stirred with ice-water and extracted with chloroform. The organic extract was washed with water, saturated sodium chloride solution, dried over anhydrous magnesium sulfate; filtered, and evaporated to 5.5 g (84%) of product. Recrystallization from absolute ethanol gave the analytical sample, mp 253°-254° C.

Workup

  1. washwashed with hexanes, in dimethylformamide (5 ml)
  2. extractionextracted with chloroform
  3. extractionThe organic extract
  4. washwas washed with water, saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to 5.5 g (84%) of product
  8. customRecrystallization from absolute ethanol
  9. customgave the analytical sample, mp 253°-254° C.

Sources & evidence

ORD record
ord-5b1acc3d86304ecda6c62fc4548f63b0
Source dataset
uspto-grants-1990_07
Patent number
US04940704

Reaction notes

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