O,O-Dipyridin-2-yl carbonothioate → 5-Cyano-7-isothiocyanato-8-methylquinoline

HRID 1901246Notes

Reaction equation

HRID 1901246 reaction equation
C1C=C(O[C:8](OC2N=CC=CC=2)=[S:9])N=CC=1.[NH2:17][C:18]1[C:27]([CH3:28])=[C:26]2[C:21]([CH:22]=[CH:23][CH:24]=[N:25]2)=[C:20]([C:29]#[N:30])[CH:19]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:29]([C:20]1[CH:19]=[C:18]([N:17]=[C:8]=[S:9])[C:27]([CH3:28])=[C:26]2[C:21]=1[CH:22]=[CH:23][CH:24]=[N:25]2)#[N:30]

Participants

5

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 184653807-Amino-5-cyano-8-methylquinoline

Product 1

HCID 184653735-Cyano-7-isothiocyanato-8-methylquinoline

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of di-2-pyridyl thionocarbonate (1.22 g) and 4-dimethylaminopyridine (0.08 g) in methylene chloride (60 mL) is added dropwise a solution of 7-amino-5-cyano-8-methylquinoline (1.22 g) in methylene chloride (80 mL). The mixture is stirred for 4 hours at room temperature then rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with 25% ethyl acetate/hexane to afford 5-cyano-8-methyl-7-quinolinylisothiocyanate as a yellow solid.

Workup

  1. customThe residue is purified by flash chromatography on silica gel
  2. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ad6763190a52401fa52f85d0950abdbb
Source dataset
uspto-grants-1996_11
Patent number
US05576437

Reaction notes

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