Dimethylformamide → 3-Chloroisoquinoline-7-carbonitrile

HRID 1465742Notes

Reaction equation

HRID 1465742 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([Cl:12])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.[Cu][C:14]#[N:15].CN(C=O)C>CCOC(C)=O>[Cl:12][C:7]1[N:8]=[CH:9][C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([C:14]#[N:15])[CH:11]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 513419807-Bromo-3-chloroisoquinolineHCID 178418546HCID 178418546, compound

Product 1

HCID 848196053-Chloroisoquinoline-7-carbonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a flask charged with 7-bromo-3-chloroisoquinoline (1.0 g, 4.1 mmol) and a stir bar was added copper(I) cyanide (550 mg, 6.2 mmol) and DMF (50 mL). The mixture was heated to 150° C. for 24 hours under an atmosphere of nitrogen. The reaction was diluted with EtOAc, washed with sat. NH4OAc and brine, dried over sodium sulfate, concentrated and purified by silica gel chromatography (Hexanes:DCM) and the solvent removed to afford the title compound. LC-MS (IE, m/z): 189 [M+1]+.

Workup

  1. washwashed with sat. NH4OAc and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (Hexanes:DCM)
  5. customthe solvent removed

Sources & evidence

ORD record
ord-17efae57b70342efa32828aeef1cd4d0
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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