Ethanol → 4-Ethoxy-1-ethyl-5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]-pyrazolo[4,3-e]pyridin-11(1H)-one

HRID 1763258Notes

Reaction equation

HRID 1763258 reaction equation
Cl[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.[Na].[CH2:24]([OH:26])[CH3:25]>>[CH2:24]([O:26][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)[CH3:25]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 5360545SodiumHCID 203820734-chloro-1-ethyl-5,6-dihydrobenzo[5,6]-cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11(1H)-one

Product 1

HCID 203820954-Ethoxy-1-ethyl-5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]-pyrazolo[4,3-e]pyridin-11(1H)-one

Procedure

6.2 g. of 4-chloro-1-ethyl-5,6-dihydrobenzo[5,6]-cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11(1H)-one (0.02 mol.), from example 1(e), are added to a solution of 0.5 g. of sodium (0.022 mol.) in 150 ml. of absolute ethanol. The mixture is heated at 120° (bath temperature) in an autoclave for four hours. After cooling, the crystallized 4-ethoxy-1-ethyl-5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11-(1H)-one is filtered off and washed with water; yield: 3.5 g. An additional crop of 2.1 g. is obtained by work up of the mother liquor, total yield: 5.6 g. (87.5%); m.p. 150°-152° (ethanol; refrigerator).

Workup

  1. temperatureThe mixture is heated at 120° (bath temperature) in an autoclave for four hours
  2. temperatureAfter cooling
  3. filtrationthe crystallized 4-ethoxy-1-ethyl-5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11-(1H)-one is filtered off
  4. washwashed with water
  5. customis obtained by work up of the mother liquor, total yield: 5.6 g

Sources & evidence

ORD record
ord-e18ced45579c4ff18eeb70f1d931178c
Source dataset
uspto-grants-1978_09
Patent number
US04111940

Reaction notes

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