Hydrogen Bromide → 3,4-Dihydroxyphenyl-3-pyridyl ketone

HRID 2418967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2418967
N1C=CC=CC=1CO.BrC1C=NC=CC=1.COC1C=C(C(C2C=NC=CC=2)O)C=CC=1OC.C[O:35][C:36]1[CH:37]=[C:38]([C:44]2[C:49]([C:50]([C:52]3[C:53]([C:58]4[CH:63]=[CH:62][C:61]([O:64]C)=[C:60]([O:66]C)[CH:59]=4)=[N:54][CH:55]=[CH:56][CH:57]=3)=[O:51])=[CH:48][CH:47]=[CH:46][N:45]=2)[CH:39]=[CH:40][C:41]=1[O:42]C.Br>>[OH:66][C:60]1[CH:59]=[C:58]([C:53]2[C:52]([C:50]([C:49]3[C:44]([C:38]4[CH:39]=[CH:40][C:41]([OH:42])=[C:36]([OH:35])[CH:37]=4)=[N:45][CH:46]=[CH:47][CH:48]=3)=[O:51])=[CH:57][CH:56]=[CH:55][N:54]=2)[CH:63]=[CH:62][C:61]=1[OH:64]

Komponenten

6

Edukt 5

HCID 260Hydrogen BromideHCID 11474PiconolHCID 122863-BromopyridineHCID 13475606(3,4-Dimethoxyphenyl)(pyridin-3-yl)methanolHCID 536816023,4-Dimethoxyphenyl-3-pyridyl ketone

Produkt 1

HCID 1364097163,4-Dihydroxyphenyl-3-pyridyl ketone

Versuchsvorschrift

3,4-Dimethoxyphenyl-3-pyridyl carbinol was obtained as an oil as described for the preceding 2-pyridyl carbinol of Example 40 except that 3-bromopyridine is used in place of 2-bromopyridine. This carbinol was converted to 3,4-dimethoxyphenyl-3-pyridyl ketone, mp 76°-78° C and reacted with hydrobromic acid to give 3,4-dihydroxyphenyl-3-pyridyl ketone, mp 182°-184° Crown ether formation as described in Example 40 gave 1-(2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16 hexaoxacyclooctadecin-18-yl)-1-(3-pyridyl)-methanone, mp 98°-100° C.

Quellen und Nachweise

ORD-Eintrag
ord-3fdc51ac73944451a16349151bf7e188
Quelldatensatz
uspto-grants-1978_08
Patentnummer
US04104275

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