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

HRID 1403746

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-a33eb3d5ed5d453989108329cbdd1d3a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912205B2

Linked notes

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