Onychine → 5H-Indeno[1,2-b]pyridin-5-ol, 4-methyl-

HRID 1683148Notes

Reaction equation

HRID 1683148 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14](=[O:15])[C:3]=12.[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[CH:14]([OH:15])[C:3]=12

Participants

4

Reactant 2

HCID 72584OnychineHCID 4311764Sodium borohydride

Product 1

HCID 111599195H-Indeno[1,2-b]pyridin-5-ol, 4-methyl-Yield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 15 g (0.0769 mol) of 4-methyl-5H-indeno[3,2-b]pyridin-5-one in 150 ml of methanol was treated in portions with 3.8 g (0.1 mol) of NaBH4 at from 0° to -5° C. After stirring at room temperature for 14 hours, the mixture was concentrated under reduced pressure. The residue was treated with 350 ml of methylene chloride and with 150 ml of a 15% strength aqueous potassium hydroxide solution and additionally stirred for 1 hour. The organic phase was separated off, washed with water, dried over Na2SO4 and concentrated to a volume of 50 ml under reduced pressure. The crystal magma was filtered off with suction at 0° C. and washed with a little diethyl ether and pentane. 9.4 g (62% of theory) of 4-methyl-5H-indeno[3,2-b]pyridin-5-ol were obtained as yellowish crystals of m.p. 154°-156° C.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe residue was treated with 350 ml of methylene chloride and with 150 ml of a 15% strength aqueous potassium hydroxide solution
  3. stirringadditionally stirred for 1 hour
  4. customThe organic phase was separated off
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to a volume of 50 ml under reduced pressure
  8. filtrationThe crystal magma was filtered off with suction at 0° C.
  9. washwashed with a little diethyl ether and pentane

Sources & evidence

ORD record
ord-94017de0365d413da25566ad7a0ef513
Source dataset
uspto-grants-1997_06
Patent number
US05637554

Reaction notes

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