Dimethylamine → Pyridazino(4,3-c)isoquinolin-6-amine, N,N-dimethyl-3-phenyl-

HRID 986750Notes

Reaction equation

HRID 986750 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[N:15]=[N:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:18][C:7]=2[N:6]=1>C(COC)OC>[C:19]1([C:17]2[N:16]=[N:15][C:8]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:5]([N:2]([CH3:3])[CH3:1])=[N:6][C:7]=3[CH:18]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 13526620HCID 13526620, compound

Product 1

HCID 13526624Pyridazino(4,3-c)isoquinolin-6-amine, N,N-dimethyl-3-phenyl-Yield 53.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Dimethylamine (6 g), 6-chloro-3-phenyl-pyridazino-[4,3-c]isoquinoline (5.83 g, 0.02 mol) and dimetoxyethane (120 ml) are heated at 120° C. for about 8 hours in a bomb. Then the reaction mixture is concentrated to dryness under reduced pressure, the residue is disaggregated with water (200 ml) and the solid recovered by filtration is dried, yielding 5.8 g of a crude product which is crystallized from acetone to give 3.2 g of the product of the title. M.p. 134°-136° C. A further crop of about 1,7 g is obtained by purifying the residue of the concentration of the mothers liquors by means of a silica gel column chromatography which uses chloroform as the eluent. Overall yield 4,9 g (81,5%).

Workup

  1. concentrationThen the reaction mixture is concentrated to dryness under reduced pressure
  2. filtrationthe solid recovered by filtration
  3. customis dried
  4. customyielding 5.8 g of a crude product which
  5. customis crystallized from acetone

Sources & evidence

ORD record
ord-b928f5519b9e4c82aed6170bc90051ac
Source dataset
uspto-grants-1987_12
Patent number
US04716159

Reaction notes

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