Phosphorus oxychloride → 1-Chloro-7-nitro-3,4-dihydroisoquinoline

HRID 969625Notes

Reaction equation

HRID 969625 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][C:11]2=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH2:8][CH2:9][N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 131528427-Nitro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 219596651-Chloro-7-nitro-3,4-dihydroisoquinoline

Procedure

Tricyclic heterocycles can be prepared by the process outlined in Scheme 7. 7-Nitro-3,4-dihydro-2H-isoquinolin-1-one 23 is heated in POCl3 at a temperature above RT, preferably at a temperature sufficient for reflux, to form the 1-chloro-7-nitro-3,4-dihydroisoquinoline 24. The 1-chloro-7-nitro-3,4-dihydroisoquinoline 24 is dissolved in a solvent, such as THF, and H2NNH2 is added. The reaction is heated with HC(OEt)3 at a temperature above RT, preferably at a temperature above about 75° C., and more preferably at a temperature at about 115° C. to give the nitro-substituted tricyclic. Hydrogenation, such as with an H2 atmosphere in the presence of a catalyst, such as Pd/C, gives 2-amino-5,6,7-trihydro-1,2,4-triazolo[3,4-a]isoquinoline 25.

Workup

  1. temperaturefor reflux

Sources & evidence

ORD record
ord-d4f34fb77fa848f6b60acf96aa9da9c8
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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