Formic Acid → HCID 86741159, compound

HRID 1249153Notes

Reaction equation

HRID 1249153 reaction equation
[NH2:1][C@@H:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[C@H:3]1[OH:16].N1C=CC=C[CH:18]=1.[OH2:23].[CH:24]([OH:26])=O>>[CH:18]([O:16][C@H:3]1[C@H:2]([NH:1][CH:24]=[O:26])[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]1([CH3:14])[CH3:15])=[O:23]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 1049PyridineHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Product 1

HCID 86741159HCID 86741159, compound

Procedure

Trans-4-amino-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol *(0.90 g) was heated under reflux in formic acid (15 ml) and pyridine (1 ml) during 19 hr. The cooled solutions 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 2 mm silica gel, flow rate 9 ml/min) to give after recrystallisation from ethyl acetate-pentane the title compound (0.15 g) as crystals of m.p. 171°-172° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationFiltration and evaporation
  5. waitleft an orange coloured oil which
  6. customwas chromatographed
  7. wash(chromatotron, ethyl acetate-pentane gradient elution on 2 mm silica gel, flow rate 9 ml/min)
  8. customto give
  9. customafter recrystallisation from ethyl acetate-pentane the title compound (0.15 g) as crystals of m.p. 171°-172° C.

Sources & evidence

ORD record
ord-7a371a65d68b4d039e28a5ee776e0905
Source dataset
uspto-grants-1986_12
Patent number
US04629734

Reaction notes

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