3-(Trifluoromethyl)aniline → 5-iodo-6-methyl-N-(3-(trifluoromethyl)phenyl)isoquinolin-1-amine

HRID 1668958Notes

Reaction equation

HRID 1668958 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([I:13])[C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[F:14][C:15]([F:24])([F:23])[C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>>[I:13][C:7]1[C:8]([CH3:12])=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][N:3]=[C:2]2[NH:19][C:18]1[CH:20]=[CH:21][CH:22]=[C:16]([C:15]([F:14])([F:23])[F:24])[CH:17]=1

Participants

3

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 58466468HCID 58466468, compound

Product 1

HCID 673385755-iodo-6-methyl-N-(3-(trifluoromethyl)phenyl)isoquinolin-1-amineYield 50%

Conditions

Temperature
140 °C

Procedure

To a solution of 1-chloro-5-iodo-6-methylisoquinoline (0.400 g, 1.32 mmol) in EPA (5.00 ml), charged to a 5 mL microwave reaction vessel, 3-(trifluoromethyl)aniline (0.329 ml, 2.64 mmol) was added. The reaction mixture was stirred at 140° C. for 20 min. The resulting ppt was collected by filtration and washed with excess IPA. The solid was dried under vacuum to give 5-iodo-6-methyl-N-(3-(trifluoromethyl)phenyl)isoquinolin-1-amine (0.282 g, 50.0% yield) as a pale solid. MS (M+H)+ 429.

Workup

  1. filtrationThe resulting ppt was collected by filtration
  2. washwashed with excess IPA
  3. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-3f75f6ea33df48268dddbb2598d9e6d4
Source dataset
uspto-grants-2011_08
Patent number
US07989461B2

Reaction notes

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