(4-Aminophenoxy)benzene → (4-Phenoxyphenyl)-(7-iodoquinolin-4-yl)amine

HRID 1403746

Reaktionsgleichung

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([I:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.IC1C=C2C(C(N)=CC=N2)=CC=1.[O:25]([C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)CCC>[O:25]([C:32]1[CH:33]=[CH:34][C:35]([NH:36][C:2]2[C:11]3[C:6](=[CH:7][C:8]([I:12])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:37][CH:38]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

4-Chloro-7-iodoquinoline (10 g, 34 mmol) [Semenov, V. P.; Studenikov, A. N. Synthesis of 7-iodo-4-aminoquinoline derivatives. Khim. Geterotsikl. Soedin. (1980), Issue 7, 972-5] and 4-phenoxyaniline (6.38 g, 34 mmol) in butanol (75 ml) were heated at gentle reflux (120° C.) overnight (18 hrs). On cooling the resultant precipitate was collected by filtration and washed with acetonitrile (2×50 ml). The resultant solid was suspended in chloroform (500 ml) and 2N sodium carbonate solution (300 ml) and heated at 75° C. for 45 mins. On cooling the resultant precipitate was collected by filtration, washed with water (2×50 ml) and dried to yield the product as a pale brown solid. (9.95 g, 66%) δ H [2H6] DMSO 8.35 (3H, m), 8.20 (1H, s), 8.10 (1H, d), 7.85 (1H, s), 7.35 (4H, m), 7.15 (4H, d), 6.75 (1H, d).

Aufarbeitung

filtrationwas collected by filtration
washwashed with acetonitrile (2×50 ml)
temperature2N sodium carbonate solution (300 ml) and heated at 75° C. for 45 mins
temperatureOn cooling the resultant precipitate
filtrationwas collected by filtration
washwashed with water (2×50 ml)
customdried

Quellen und Nachweise

ORD-Eintrag: ord-a33eb3d5ed5d453989108329cbdd1d3a
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08912205B2

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