Triethylamine → 4-Chloro-1-ethyl-1,5,6,11-tetrahydrobenzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11-ol

HRID 1763257Notes

Reaction equation

HRID 1763257 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[N:9][N:10]([CH2:11][CH3:12])[C:6]=2[N:5]=[C:4]2[C:13](=[O:22])[C:14]3[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=3[CH2:16][CH2:17][C:3]=12.C(N(CC)CC)C.C(OCC)(=O)C>[Pd].C(O)C>[Cl:1][C:2]1[C:7]2[CH:8]=[N:9][N:10]([CH2:11][CH3:12])[C:6]=2[N:5]=[C:4]2[CH:13]([OH:22])[C:14]3[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=3[CH2:16][CH2:17][C:3]=12

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 203820734-chloro-1-ethyl-5,6-dihydrobenzo[5,6]-cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11(1H)-one

Product 1

HCID 203820924-Chloro-1-ethyl-1,5,6,11-tetrahydrobenzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

20.2 g. of 4-chloro-1-ethyl-5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11(1H)-one (0.065 mol.) and 13 g. of triethylamine (0.13 mol.), dissolved in 400 ml. of ethyl acetate and 75 ml. of absolute ethanol, are catalytically hydrogenated in the presence of 2 g. of palladium on charcoal (10%) at room temperature. In about 6 hours, the theoretical amount of hydrogen is absorbed. The catalyst is then filtered off, the filtrate evaporated in vacuo and the residue extracted with 200 ml. of ether. The ethereal extract is washed with water, dried with Na2SO4 and the ether removed. The resulting material is recrystallized from petroleum ether (60°-70°) to yield 12.7 g. (62.5%) of 4-chloro-1-ethyl-1,5,6,11-tetrahydro[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11-ol; m.p. 128°-130°.

Workup

  1. customat room temperature
  2. customthe theoretical amount of hydrogen is absorbed
  3. filtrationThe catalyst is then filtered off
  4. customthe filtrate evaporated in vacuo
  5. extractionthe residue extracted with 200 ml
  6. extractionThe ethereal extract
  7. washis washed with water
  8. dry with materialdried with Na2SO4
  9. customthe ether removed
  10. customThe resulting material is recrystallized from petroleum ether (60°-70°)
  11. customto yield 12.7 g

Sources & evidence

ORD record
ord-e9cace86f63946dea1f44f8f64cf074f
Source dataset
uspto-grants-1978_09
Patent number
US04111940

Reaction notes

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