5H-(1)Benzopyrano(4,3-c)pyridine, 1,2,3,4-tetrahydro-5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy- → 5,5-Dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-5H-[1]benzopyrano[3,4-d]pyridine

HRID 126796

Reaction equation

HRID 126796 reaction equation
[CH3:1][C:2]1([CH3:26])[C:21]2[CH2:22][CH2:23][NH:24][CH2:25][C:20]=2[C:5]2[C:6]([OH:19])=[CH:7][C:8]([CH:10]([CH:12]([CH3:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:11])=[CH:9][C:4]=2[O:3]1>[Pd].C1(C)C(C)=CC=CC=1>[CH3:26][C:2]1([CH3:1])[C:21]2=[CH:22][CH:23]=[N:24][CH:25]=[C:20]2[C:5]2[C:6]([OH:19])=[CH:7][C:8]([CH:10]([CH:12]([CH3:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:11])=[CH:9][C:4]=2[O:3]1

Participants

4

Reactant 1

HCID 2135435H-(1)Benzopyrano(4,3-c)pyridine, 1,2,3,4-tetrahydro-5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy-

Product 1

HCID 197814025,5-Dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-5H-[1]benzopyrano[3,4-d]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 4.20 g. of 5,5-dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine, 0.8 g. of 10% palladium on carbon and 80 ml. of xylene was stirred and refluxed for 25 hours. After cooling, the catalyst was removed by filtration. The filtrate was evaporated in vacuo and the product was recrystallized from autonitrile; m.p. 155°-157°.

Workup

  1. additionA mixture of 4.20 g
  2. temperaturerefluxed for 25 hours
  3. temperatureAfter cooling
  4. customthe catalyst was removed by filtration
  5. customThe filtrate was evaporated in vacuo
  6. customthe product was recrystallized from autonitrile

Sources & evidence

ORD record
ord-62e66fd39837453fa9f80da2252cafb7
Source dataset
uspto-grants-1981_03
Patent number
US04254116

Linked notes

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