Hydroxylamine → HCID 15634849, compound

HRID 1979550Notes

Reaction equation

HRID 1979550 reaction equation
N[OH:2].[C:3]([C:5]1[CH:17]=[CH:16][C:8]2[O:9][C:10]([CH3:15])([CH3:14])[CH:11]3[O:13][CH:12]3[C:7]=2[CH:6]=1)#[N:4].[OH-].[NH4+].[N:20]1[CH:25]=CC=CC=1>C(O)=O.O>[C:3]([C:5]1[CH:17]=[CH:16][C:8]2[O:9][C:10]([CH3:15])([CH3:14])[C@@H:11]([OH:13])[C@H:12]([NH:20][CH:25]=[O:2])[C:7]=2[CH:6]=1)#[N:4]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 1049PyridineHCID 14923Ammonium HydroxideHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Product 1

HCID 15634849HCID 15634849, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

The aminoalcohol (0.9 g), obtained by stirring 6-cyano-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-benzo[b]pyran with ethanolic ammonium hydroxide), was heated under reflux in formic acid (15 ml) and pyridine (1 ml) during 19 hr. The cooled solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulphate. Filtration and evaporation left an orange coloured oil which was chromatographed (chromatotron, ethyl acetate-pentane gradient elution on silica gel 2 mm, flow rate 9 ml/min.) to give after one recrystallisation from ethyl acetate, the title compound (220 mg), of m.p. 228.5°-230.5° C.

Workup

  1. temperaturewas heated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationFiltration and evaporation
  6. waitleft an orange coloured oil which
  7. customwas chromatographed
  8. wash(chromatotron, ethyl acetate-pentane gradient elution on silica gel 2 mm, flow rate 9 ml/min.)
  9. customto give
  10. customafter one recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-222ed52a97174c97a4e5ad63bcada039
Source dataset
uspto-grants-1984_11
Patent number
US04481214

Reaction notes

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