Tributylvinyltin → 2-(4-Hydroxyphenyl)-4-vinylquinolin-6-ol

HRID 1867480

Reaction equation

HRID 1867480 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:3]=1.[CH2:20]([Sn](CCCC)(CCCC)C=C)[CH2:21]CC>>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:4]2[CH:3]=[C:2]([CH:20]=[CH2:21])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=3)[N:5]=2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 81998TributylvinyltinHCID 1354548024-Bromo-2-(4-hydroxyphenyl)quinolin-6-ol

Product 1

HCID 1354097292-(4-Hydroxyphenyl)-4-vinylquinolin-6-olYield 69%

Procedure

This compound was prepared from 6a and tributyl(vinyl)tin according to method J. Yellow solid; Yield: 69%; mp>200° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 5.69 (d, J=11.7 Hz, 1H), 6.23 (dd, J=18.3, 1.0 Hz, 1H), 6.90 (d, J=8.5 Hz, 2H), 7.31 (dd, J=9.0, 2.7 Hz, 1H), 7.35 (d, J=2.2 Hz, 1H), 7.40 (dd, J=17.3, 11.0 Hz, 1H), 7.88 (d, J=8.8 Hz, 1H), 8.01 (s, 1H), 8.11 (d, J=8.8 Hz, 2H), 9.73 (s, 1H), 9.98 (s, 1H); MS (ESI) m/z 262 ([M−H]−), 264 ([M+H]+); Anal. Calcd for C17H13NO2: C, 77.55; H, 4.98; N, 5.32. Found: C, 74.26; H, 5.38; N, 4.82.

Sources & evidence

ORD record
ord-0fad802cc5a14fd0a32fdaf157dbba02
Source dataset
uspto-grants-2009_12
Patent number
US07632845B2

Linked notes

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