N-bromobutanimide → 6-bromo-7-hydroxy-3,4,4a,8a-tetrahydro-1H-quinolin-2-one

HRID 44182Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][CH:5]2[CH:10]([CH:11]=1)[NH:9][C:8](=[O:12])[CH2:7][CH2:6]2.C1C(=O)N([Br:20])C(=O)C1>>[Br:20][C:3]1[C:2]([OH:1])=[CH:11][CH:10]2[CH:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)[CH:4]=1

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 67152391HCID 67152391, compound

Product 1

HCID 669113116-bromo-7-hydroxy-3,4,4a,8a-tetrahydro-1H-quinolin-2-one

Procedure

This intermediate was obtained according to general procedure I from 7-hydroxy-3,4,4a,8a-tetrahydro-1H-quinolin-2-one (370 mg, 2.27 mmol) and NBS (424 mg, 2.38 mmol) after flash chromatography on silica gel (hexanes/ethyl acetate, 1/1, Rf=0.15) as white solid (500 mg, 2.07 mmol, 91%).

Workup

customThis intermediate was obtained

Sources & evidence

ORD record: ord-8ec8940afebb474fb983513d139ac7bc
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541404B2

Reaction notes

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