Ethylenediamine monohydrate → 5-Cyano-6-methoxy-2-methylthioquinoline

HRID 456994Notes

Reaction equation

HRID 456994 reaction equation
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:14][CH3:15])=[N:7]2.[C:16]([Cu])#[N:17].O.C(N)CN>CN(C=O)C>[C:16]([C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:14][CH3:15])=[N:7]2)#[N:17]

Participants

5

Reactant 3

HCID 12200817Ethylenediamine monohydrateHCID 221396965-Bromo-6-methoxy-2-methylthioquinolineHCID 178418546HCID 178418546, compound

Product 1

HCID 221396835-Cyano-6-methoxy-2-methylthioquinolineYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-bromo-6-methoxy-2-methylthioquinoline (6.1 g, 21 mmol) and CuCN (3.7 g, 41 mmol) in DMF (80 mL) was heated at 150° C. for 14 hours. The mixture was cooled and treated sequentially with 2:1 H2O/ethylenediamine (15 mL). The mixture was extracted with 1:1 EtOAc/hexane. The organic layer was worked-up. HPLC (1:8 EtOAc/hexane) gave 4.2 g (87%) of 5-cyano-6-methoxy-2-methylthioquinoline as a light yellow solid, (M+) 230(100).

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with 1:1 EtOAc/hexane

Sources & evidence

ORD record
ord-33562d86b260436da6d44cbeb7a3fa0d
Source dataset
uspto-grants-2007_03
Patent number
US07186840B2

Reaction notes

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