Sodium Hydroxide → HCID 13134787, compound

HRID 355113Notes

Reaction equation

HRID 355113 reaction equation
[C:1]([CH2:3][C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[C:14]([CH2:15][C:16]([OH:18])=O)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:6][CH:5]=1)#[N:2].[OH-:21].[Na+]>>[O:18]=[C:16]1[CH2:15][C:14]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=2[O:8][C:7]2[CH:19]=[CH:20][C:4]([CH2:3][C:1]([NH2:2])=[O:21])=[CH:5][C:6]1=2

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 53878494HCID 53878494, compound

Product 1

HCID 13134787HCID 13134787, compoundYield 30%

Procedure

To 1 g of 2-(4-cyanomethylphenoxy)-3-pyridylacetic acid was added 20 g of polyphosphoric acid, and the mixture was stirred in an oil bath at 151°-152° C. for 2.5 hours. After cooling, to this was ice water to decompose excess polyphosphoric acid, and the mixture was basified with a 10% sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with water and then a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by distillation to obtain a solid, which was chromatographed over 20 g of silica gel and eluted with n-hexane/acetone (2/1-1/1) to obtain crystals. These were recrystallized from acetone to give 300 mg (yield: 30%) of (5,6-dihydro-6-oxo benzo[b]pyrido-[3,2-f]oxepin-8-yl)-acetamide as white needle crystals having a melting point of 214°-217° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materiala saturated sodium chloride solution and dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation
  5. customto obtain a solid, which
  6. customwas chromatographed over 20 g of silica gel
  7. washeluted with n-hexane/acetone (2/1-1/1)
  8. customto obtain crystals
  9. customThese were recrystallized from acetone

Sources & evidence

ORD record
ord-afa5811deef744a5a8d01fe105534309
Source dataset
uspto-grants-1983_03
Patent number
US04377702

Reaction notes

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