Chlorosuccinimide → 4-Chloroisoquinolin-3-amine

HRID 1876007Notes

Reaction equation

HRID 1876007 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH2:11])[N:2]=1.[Cl:12]N1C(=O)CCC1=O>CO>[Cl:12][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=[N:2][C:3]=1[NH2:11]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 311869Isoquinolin-3-Amine

Product 1

HCID 231225434-Chloroisoquinolin-3-amineYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To isoquinolin-3-amine (2.02 g, 14.0 mmol) in methanol (60 mL) was added N-chlorosuccinimide (2.19 g, 16.4 mmol) at room temperature. The reaction was stirred at room temperature for 3 hours, then concentrated in vacuo. The crude material was chromatographed (Biotage: 10-100% ethyl acetate/hexanes) to yield 4-chloroisoquinolin-3-amine (2.1 g, 11.8 mmol, 84% yield) as a solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.86 (s, 1H), 7.93 (d, J=7.6 Hz, 1H), 7.79 (d, J=8.5 Hz, 1H), 7.68 (td, J=6.7, 1.8 Hz, 1H), 7.24-7.35 (m, 1H), 6.32 (br. s., 2H). MS (LC/MS) R.T.=1.50; [M+H]+=178.96.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude material was chromatographed (Biotage: 10-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a2425a823c2a4d4bbaa53fa63acc44a4
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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