Pyrazolo(5,1-a)isoquinoline, 5,6-dihydro-2-(3-methoxyphenyl)- → Pyrazolo(5,1-a)isoquinoline, 2-(m-methoxyphenyl)-

HRID 616721Notes

Reaction equation

HRID 616721 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:21]=[C:12]3[C:13]4[C:18]([CH2:19][CH2:20][N:11]3[N:10]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:6]=[CH:7][CH:8]=1>O=[Mn]=O.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:21]=[C:12]3[C:13]4[C:18]([CH:19]=[CH:20][N:11]3[N:10]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 3045616Pyrazolo(5,1-a)isoquinoline, 5,6-dihydro-2-(3-methoxyphenyl)-

Product 1

HCID 3045617Pyrazolo(5,1-a)isoquinoline, 2-(m-methoxyphenyl)-

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 2.5 g. of 2-(m-methoxyphenyl)-5,6-dihydro-pyrazolo[5,1-a]isoquinoline in 100 ml. of benzene is gradually added with stirring 30 g. of MnO2 prepared as described by E. Pratt et al., J. Org. Chem. 26, 2973 (1961) and activated according to the procedure of J. M. Goldman, J. Org. Chem. 34, 1979 (1969). The obtained mixture is refluxed with stirring for five days, then filtered. The filtrate after evaporation and crystallization of the solid residue from isopropyl ether gives 1 g. of the title product, m.p. 109°-11° C.

Workup

  1. temperatureThe obtained mixture is refluxed
  2. stirringwith stirring for five days
  3. filtrationfiltered
  4. customThe filtrate after evaporation and crystallization of the solid residue from isopropyl ether
  5. customgives 1 g

Sources & evidence

ORD record
ord-d765ab1f51f54d80a2975aae4695cbcd
Source dataset
uspto-grants-1978_02
Patent number
US04075342

Reaction notes

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