Epichlorohydrin → 5-[(Oxiran-2-yl)methoxy]-3,4-dihydroquinolin-2(1H)-one

HRID 1903077Notes

Reaction equation

[CH2:1]1[C:7]2[C:8]([OH:12])=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:3](=[O:4])[CH2:2]1.[CH2:13]([CH:15]1[O:17][CH2:16]1)Cl>>[O:17]1[CH2:16][CH:15]1[CH2:13][O:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]2[C:7]=1[CH2:1][CH2:2][C:3](=[O:4])[NH:5]2

Participants

Reactant 2

HCID 7835Epichlorohydrin

HCID 1691533,4-Dihydro-5-hydroxy-2(1H)-quinolinone

Product 1

HCID 128994235-[(Oxiran-2-yl)methoxy]-3,4-dihydroquinolin-2(1H)-one

Procedure

5-Hydroxy-3,4-dihydro-2-quinoline (prepared in three steps from cyclohexane-1,3-dione and acrylonitrile) is allowed to react with epichlorohydrin to give 5-(2,3-epoxypropoxy)-3,4-dihydro-2-quinolinone [J. Med. Chem. 17,529 (1974)].

Sources & evidence

ORD record: ord-658d4f8f2a8741f685d328a753c524a7
Source dataset: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04435397

Reaction notes

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