1-Chloro-5-nitroisoquinoline → HCID 86692253, compound

HRID 1469765Notes

Reaction equation

HRID 1469765 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]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:17]=1[NH2:18]>CN1CCCC1=O>[F:15][C:16]1[CH:22]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:20]=[CH:19][C:17]=1[NH:18][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

Participants

4

Reactant 2

HCID 4597741-Chloro-5-nitroisoquinolineHCID 27376742-Fluoro-4-(trifluoromethyl)aniline

Product 1

HCID 86692253HCID 86692253, compoundYield 46.7%

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, 250 mg, 1.19 mmol), and 2-fluoro-4-(trifluoromethyl)aniline (330 mg, 1.84 mmol) in N-methylpyrrolidinone (2 mL) to afford 195 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 9.69 (s, 1H), 8.84 (d, J=7.8 Hz, 1H), 8.55 (d, J=7.8 Hz, 1H), 8.15 (d, J=5.7 Hz, 1H), 7.86-7.57 (m, 5H); MS (m/z): 352.18 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-443d7901eae245bcbef3bd4454cb6504
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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