Oxalyl chloride → 6-chloro-4-(3-hydroxyphenyl)-3-(3-methyl-isoxazol-5-yl)-1H-quinolin-2-one

HRID 2053423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053423
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1)=O.[CH3:18][C:19]1[CH:23]=[C:22]([CH2:24][C:25](Cl)=[O:26])[O:21][N:20]=1.Cl.CC1C=C(CC(O)=O)ON=1.C(Cl)(=O)C(Cl)=O>C(Cl)Cl.C(N(CC)CC)C.CN(C)C=O>[Cl:17][C:14]1[CH:13]=[C:3]2[C:2](=[CH:16][CH:15]=1)[NH:1][C:25](=[O:26])[C:24]([C:22]1[O:21][N:20]=[C:19]([CH3:18])[CH:23]=1)=[C:4]2[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1

Komponenten

8

Edukt 4

HCID 65578Oxalyl chlorideHCID 2794900(2-Amino-5-chlorophenyl)(3-hydroxyphenyl)methanoneHCID 123668732-(3-Methylisoxazol-5-yl)acetyl chlorideHCID 67010666(3-Methyl-isoxazol-5-yl)-acetic acid hydrochloride

Produkt 1

HCID 1354970676-chloro-4-(3-hydroxyphenyl)-3-(3-methyl-isoxazol-5-yl)-1H-quinolin-2-oneAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-5-chloro-3′-hydroxybenzophenone (0.1 g, 0.4 mmol), (3-methyl-isoxazol-5-yl)-acetyl chloride (1.18 mmol) [synthesized from the reaction between (3-methyl-isoxazol-5-yl)-acetic acid hydrochloride and oxalyl chloride catalyzed by N,N-dimethylformamide in DCM], triethylamine (Et3N) (0.20 mL) and DCM (10 mL) was heated to reflux overnight. The mixture was then cooled to room temperature and concentrated, and the residue was purified by flash chromatography on silica gel (5% methanol in DCM) to give 6-chloro-4-(3-hydroxyphenyl)-3-(3-methyl-isoxazol-5-yl)-1H-quinolin-2-one (99 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ 9.68 (s, 1H), 7.68-7.60 (m, 2H), 7.43 (d, J=10.0 Hz, 1H), 7.25 (t, J=10.0 Hz, 1H), 7.01-6.97 (m, 1H), 6.88-6.80 (m, 1H), 6.68-6.59 (m, 1H), 6.47 (s, 1H), 2.15 (s, 3H). MS: 353.2 (M+H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography on silica gel (5% methanol in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-c15a2c0a8f134028be82db83641f9d26
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326788B2

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