Azane;hydrate → HCID 20338060, compound

HRID 1395769Notes

Reaction equation

HRID 1395769 reaction equation
[C:1]([CH:3]([C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[O:8][C:9]1[C:14]([CH2:15][C:16]([OH:18])=O)=[CH:13][CH:12]=[CH:11][N:10]=1)[CH3:4])#[N:2].[OH2:22].N>>[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:6]=[C:5]([CH:3]([CH3:4])[C:1]([NH2:2])=[O:22])[CH:21]=[CH:20][C:19]1=2

Participants

3

Reactant 2

HCID 12896473Azane;hydrateHCID 20338035HCID 20338035, compound

Product 1

HCID 20338060HCID 20338060, compound

Conditions

Temperature
150 °C

Procedure

The mixture of 1.3 g of 2-[3'-(α-cyanoethyl)-phenoxy]-3-pyridylacetic acid and 30 g of polyphosphoric acid was stirred at 150° C. for 2 hours. After cooling, to this was added ice-water and the mixture was alkalified with 10% ammonia water and extracted with chloroform. The extract was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain the oil, which was chromatographed over silica gel, eluted with chloroform/ethanol (50/1), and there was obtained a solid substance. This was recrystallized from methanol to give 250 mg of 2-(5,6-dihydro-6-oxo benzo[b]pyrido[3,2-f]oxepin-9-yl)-propionamide as pale yellow powder having a melting point of 89°-90° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with chloroform
  3. washThe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customto obtain the oil, which
  7. customwas chromatographed over silica gel
  8. washeluted with chloroform/ethanol (50/1)
  9. customthere was obtained a solid substance
  10. customThis was recrystallized from methanol

Sources & evidence

ORD record
ord-9b8f41eedaa4442086a43842ac83094a
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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