Dichloromethane → 2-Benzoyl-5-bromo-1-cyano-1,2-dihydroisoquinoline

HRID 2192468Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.ClCCl.C[Si]([C:19]#[N:20])(C)C.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>[Cl-].[Al+3].[Cl-].[Cl-].O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:28])[CH:7]2[C:19]#[N:20]

Participants

Conditions

Temperature: 30 °C

Procedure

A round bottomed flask was charged with 5-bromoisoquinoline (available from Aldrich; 4 g, 19.2 mmol), dichloromethane (DCM) (50 ml), trimethylsilyl cyanide (4.81 ml, 38.5 mmol) and aluminium chloride (15 mg, 0.112 mmol). To the mixture was added benzoyl chloride (4.46 ml, 38.5 mmol) slowly over a period of 5 minutes. The mixture was warmed to 30° C. for 3 h after which time it was treated with water (50 ml) and stirred at room temperature for 30 minutes. The organic layers were collected and washed sequentially with 2N HCl, 2N NaOH and brine. The organic layers were passed through a hydrophobic frit before being concentrated in vacuo to give an orange solid. The solid was triturated with diethyl ether and the slurry filtered. The isolated solid was dried in vacuo to give the title compound as a grey solid (3.9 g).

Workup

customThe organic layers were collected
washwashed sequentially with 2N HCl, 2N NaOH and brine
concentrationbefore being concentrated in vacuo
customto give an orange solid
customThe solid was triturated with diethyl ether
filtrationthe slurry filtered
customThe isolated solid was dried in vacuo

Sources & evidence

ORD record: ord-3f48117fbc224cc8a1811c99ceec2977
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329730B2

Reaction notes

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