3-(Trifluoromethyl)aniline → HCID 86692221, compound

HRID 1469704Notes

Reaction equation

HRID 1469704 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20]>CN1CCCC1=O.O>[N+:12]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][N:3]=[C:2]2[NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[C:17]([C:16]([F:15])([F:24])[F:25])[CH:18]=1)([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 4597741-Chloro-5-nitroisoquinoline

Product 1

HCID 86692221HCID 86692221, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1-chloro-5-nitroisoquinoline (1.0 g, 4.8 mmol) in N-methylpyrrolidinone (2 mL) was added 3-(trifluoromethyl)aniline (917 mg, 5.7 mmol). The reaction mass was heated at 110° C. for 2 h. The reaction mass was diluted with water and was extracted with chloroform. The organic layer was dried, filtered, concentrated and purified by column chromatography to afford 1.2 g of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.44 (d, J=7.8 Hz, 1H), 8.33-8.29 (m, 2H), 7.96-7.89 (m, 3H), 7.68 (t, J=8.1 Hz, 1H), 7.51 (t, J=7.8 Hz, 1H), 7.36 (d, J=7.8 Hz, 1H), 7.26 (m, 1H).

Workup

  1. extractionwas extracted with chloroform
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-508af589647f4cde87644b8b029c3d2b
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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