Dimethylamine → 3-(Dimethylamino)isoquinolin-5-amine

HRID 1181430Notes

Reaction equation

HRID 1181430 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-])=O)[CH:8]=[CH:7][CH:6]=2.[CH3:15][NH:16][CH3:17]>>[CH3:15][N:16]([CH3:17])[C:2]1[N:3]=[CH:4][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([NH2:12])[C:10]=2[CH:11]=1

Participants

3

Reactant 2

HCID 674Dimethylamine2×HCID 167480003-Chloro-5-nitroisoquinoline

Product 1

HCID 695230323-(Dimethylamino)isoquinolin-5-amineYield 59%

Conditions

Temperature
100 °C

Procedure

3-Chloro-5-nitroisoquinoline (Description 108, 160 mg, 0.767 mmol) was dissolved in 33% ethanolic dimethylamine (6 ml) and the mixture then heated in a sealed tube at 100° C. for 2.5 h. After cooling to room temperature the solvent and excess dimethylamine was evaporated and the residue reduced according to the procedure of Description 45 to give the title compound (85 mg, 59%).

Workup

  1. customwas evaporated

Sources & evidence

ORD record
ord-d328223bdf46448c8145562582492f5a
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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