Potassium thiocyanate → 5-Methyl-2-thiocyanato-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900748Notes

Reaction equation

BrC[CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.[S-:18][C:19]#[N:20].[K+]>CN(C)C=O>[CH3:15][C:13]1[CH:14]=[C:5]2[CH2:4][CH:3]([S:18][C:19]#[N:20])[O:17][C:6]2=[C:7]2[C:12]=1[NH:11][C:10](=[O:16])[CH:9]=[CH:8]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (0.882 g), potassium thiocyanate (2.915 g) and dimethylformamide (40 ml) was stirred in a hot bath at 100° C. for 5 hours. The solvent was distilled off under reduced pressure. The residue was combined with water and extracted with chloroform. The chloroform extract liquid was washed with water, dried and condensed. The residue was crystallized from chloroform--n-hexane to obtain 0.683 g of the title compound as white powder (mp.: 227°-229° C. (dec.)).

Workup

distillationThe solvent was distilled off under reduced pressure
extractionextracted with chloroform
extractionThe chloroform extract liquid
washwas washed with water
customdried
customcondensed
customThe residue was crystallized from chloroform

Sources & evidence

ORD record: ord-4bfa96b190d2450ab2312c1ced0a2472
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576324

Reaction notes

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