1-Bromohexane → 2-Hydroxyquinoline

HRID 1768531Notes

Reaction equation

[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])O[C:2]2=O.[CH2:13](Br)CCCCC>>[NH:6]1[C:7]2[C:1](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:2]=[CH:13][C:5]1=[O:12]

Participants

Reactant 2

HCID 81011-Bromohexane

HCID 8359Isatoic Anhydride

Product 1

HCID 60382-Hydroxyquinoline

Procedure

Following the procedure set forth in Steps (2) to (4) of Preparation A, isatoic anhydride was reacted with hexyl bromide to give 1-hexyl-4-hydroxy-(2(1H)-quinolinone. That the expected product was obtained was confirmed by the spectral data: MS: role 245 (M·+); NMR (DMSO): δ0.9 (t, 3H, CH3 --CH2 --), 4.06 (t, 2H, N--OH2), 6.18 (s, 1H, =CH), 11.87 (br, 1H, OH) ppm.

Sources & evidence

ORD record: ord-3618e82ea889410eb8880cde70794958
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05378694

Reaction notes

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