Chloral Hydrate → Acetamide, 2-(hydroxyimino)-N-phenyl-

HRID 528673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528673
N1C2C(=CC=CC=2)C(C(O)=O)=CC=1.[NH:14]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:17](=O)[C:15]1=[O:16].NC1C=CC=CC=1.ClC(Cl)(Cl)C(O)O.Cl.[NH2:40][OH:41]>>[CH:21]1[CH:20]=[CH:19][C:24]([NH:14][C:15](/[CH:17]=[N:40]/[OH:41])=[O:16])=[CH:23][CH:22]=1

Komponenten

6

Edukt 5

HCID 2707Chloral HydrateHCID 6115AnilineHCID 7054IsatinHCID 102434-Quinolinecarboxylic acidHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 6861488Acetamide, 2-(hydroxyimino)-N-phenyl-

Versuchsvorschrift

The quinoline-4-carboxylic acid [E] can be prepared using the classical Sandmeyer isatin synthesis followed by the Pfitzinger reacton. The aniline was reacted with chloral hydrate and hydroxylamine hydrochloride to afford the substituted isonitrosoacetanilide which was cyclized using a suitable acid catalyst to afford the isatin as described in. Alternatively the isatin can be bought from commercial sources. The isatin can then be converted into the corresponding substituted quinoline-4-carboxylic acid using the Pfitzinger reaction as in reference 17. In some instances the Pfitzinger reaction yielded a quinoline-2,4-dicarboxylic acid which was decarboxylated to the quinoline-4-carboxylic acid by reacting it in water for 2 h using a pressured tube at 200° C.

Quellen und Nachweise

ORD-Eintrag
ord-b472b2add2f040e2bc9bb3e4ecd0d4ac
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346814B2

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