O,O-Dipyridin-2-yl carbonothioate → 8-Methyl-7-quinolinylisothiocyanate

HRID 861927Notes

Reaction equation

HRID 861927 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)=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:28][C:27]1[C:18]([N:17]=[C:8]=[S:9])=[CH:19][CH:20]=[C:21]2[C:26]=1[N:25]=[CH:24][CH:23]=[CH:22]2

Participants

5

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 14115670HCID 14115670, compound

Product 1

HCID 120495658-Methyl-7-quinolinylisothiocyanate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of di-2-pyridyl thionocarbonate (DPT) (2.29 g) (Aldrich) and 4-dimethylaminopyridine (DMAP)(0.02 g) in CH2Cl2 (50 mL) is added dropwise a solution of 7-amino-8-methylquinoline (1.3 g) in CH2Cl2 (50 mL). The mixture is stirred for 5 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 8-methyl-7-quinolinylisothiocyanate as a pale 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-c52b17eeba6442f89fc67ef42565de32
Source dataset
uspto-grants-1998_02
Patent number
US05716966

Reaction notes

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