Sodium borohydride → HCID 15280226, compound

HRID 1647247Notes

Reaction equation

HRID 1647247 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:19]=[CH:18][C:7]2[C:8](=[O:17])[C:9]3[C:14]([CH2:15][O:16][C:6]=2[CH:5]=1)=[CH:13][CH:12]=[CH:11][N:10]=3>C(O)C>[Cl:3][C:4]1[CH:19]=[CH:18][C:7]2[CH:8]([OH:17])[C:9]3[C:14]([CH2:15][O:16][C:6]=2[CH:5]=1)=[CH:13][CH:12]=[CH:11][N:10]=3

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15280224HCID 15280224, compound

Product 1

HCID 15280226HCID 15280226, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add sodium borohydride (0.96 g, 25.4 mmole) to 8-chloro[1]benzoxepino[4,3-b]pyridin-11-one (10.00 g, 40.7 mmole) in ethanol (100 mL). Stir for 18 hours at room temperature. Add water (100 mL), and concentrate in vacuo. Add additional water (100 mL), and extract with dichloromethane. Wash the organic solution with saturated NaCl, dry with MgSO4, filter, and concentrate in vacuo. Dissolve the oil in dichloromethane, and chromatograph on silica gel, eluting with 50% ethyl acetate in hexane. Combine the appropriate fractions, and concentrate under reduced pressure to give a white solid (8.50 g, 84% yield): mp 105°-108° C.

Workup

  1. concentrationAdd water (100 mL), and concentrate in vacuo
  2. additionAdd additional water (100 mL)
  3. extractionextract with dichloromethane
  4. washWash the organic solution with saturated NaCl
  5. dry with materialdry with MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. dissolutionDissolve the oil in dichloromethane
  9. washchromatograph on silica gel, eluting with 50% ethyl acetate in hexane
  10. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-e93fbc7317bf44db960518e6992a5706
Source dataset
uspto-grants-1995_07
Patent number
US05430032

Reaction notes

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