Cyanogen Bromide → 2-Cyanoaminomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

HRID 1900869Notes

Reaction equation

[NH2:1][CH2:2][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.[N:18]#[C:19]Br>O1CCCC1>[C:19]([NH:1][CH2:2][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)#[N:18]

Participants

Conditions

Temperature: 40 °C

Procedure

2-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (1.0 g, 4.34 mmol) was dissolved in tetrahydrofuran (120 ml), to which cyanogen bromide (2.76 g, 26 mmol) was added and the mixture was stirred at 40° C. for 4 hours. After completion of the reaction, the precipitated crystals were collected by filtration, and washed with water. As a result, 0.427 g of the title compound was obtained as yellow crystals (38.5%). Recrystallization from chloroform-methanol yielded the title compound as pale yellow needles (mp: 227°-230° C. (dec.)).

Workup

additionwas added
customAfter completion of the reaction
filtrationthe precipitated crystals were collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-2363675ac3f349609c479d8791810921
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576324

Reaction notes

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