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

HRID 2192468
Notes
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Reaction equation

HRID 2192468 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 82115Trimethylsilyl cyanideHCID 7364875-Bromoisoquinoline

Product 1

HCID 112677672-Benzoyl-5-bromo-1-cyano-1,2-dihydroisoquinolineYield 59.9%

Reagents, catalysts & solvents 2

HCID 6451240
Aluminum(III) Chloride
Catalyst
HCID 962WaterSolvent

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

  1. customThe organic layers were collected
  2. washwashed sequentially with 2N HCl, 2N NaOH and brine
  3. concentrationbefore being concentrated in vacuo
  4. customto give an orange solid
  5. customThe solid was triturated with diethyl ether
  6. filtrationthe slurry filtered
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes