4-(Trifluoromethyl)aniline → HCID 71678546, compound

HRID 1469767Notes

Reaction equation

HRID 1469767 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:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>CN1CCCC1=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:21][C:20]1[CH:22]=[CH:23][C:17]([C:16]([F:15])([F:24])[F:25])=[CH:18][CH:19]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 4597741-Chloro-5-nitroisoquinoline

Product 1

HCID 71678546HCID 71678546, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The title compound was prepared following the procedure described in Intermediate-1, step-2 using 1-chloro-5-nitroisoquinoline (Intermediate-1, step-1, 500 mg, 2.30 mmol), and 4-(trifluoromethyl)aniline (772 mg, 4.70 mmol) in N-methylpyrrolidinone (3 mL) to afford 750 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 9.83 (s, 1H), 8.94 (d, J=8.4 Hz, 1H), 8.53 (d, J=7.2 Hz, 1H), 8.26 (d, J=6.3 Hz, 1H), 8.06 (d, J=9.0 Hz, 2H), 8.33 (t, J=7.8 Hz, 1H), 7.66 (m, 3H); MS (m/z): 334.19 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-11bbdf4576bb4d0188fe57844ed6a318
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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