4-Chloroaniline → 1-(4-Chloroanilino)-4-[2-(pyridin-3-yl)-ethyl]-isoquinoline

HRID 49210Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:4][N:3]=1.[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.Cl.O1CCOCC1>C(O)C>[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:4][N:3]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Under an N2 atmosphere, 250 mg (0.93 mmol) of 1-chloro-4-(2-pyridin-3-yl-ethyl)-isoquinoline in 2.9 ml of abs. ethanol are mixed with 131 mg (1.02 mmol) of 4-chloro-aniline and 0.23 ml of 4 N HCl/dioxane, and stirred for 8 h at 80° C. The mixture is cooled to RT, filtered and the residue washed with acetonitrile. The residue is dissolved in 4 ml of water, then 0.9 ml of sat. NH3 solution are added, stirring is effected for 10 min, the precipitate is filtered off and washed with water. Recrystallisation from acetonitrile yields 1-(4-chloroanilino)-4-[2-(pyridin-3-yl)-ethyl]-isoquinoline; m.p.157-158° C.

Workup

temperatureThe mixture is cooled to RT
filtrationfiltered
washthe residue washed with acetonitrile
dissolutionThe residue is dissolved in 4 ml of water
addition0.9 ml of sat. NH3 solution are added
stirringstirring
waitis effected for 10 min
filtrationthe precipitate is filtered off
washwashed with water
customRecrystallisation from acetonitrile

Sources & evidence

ORD record: ord-963bb5afcf2a435197848a033b661a60
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706731B2

Reaction notes

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