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

HRID 51110

反応式

HRID 51110 の反応式
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

参加物

5

反応物 3

HCID 8764(4-Aminophenoxy)benzeneHCID 30825174-Amino-7-iodoquinolineHCID 105895404-Chloro-7-iodoquinoline

生成物 1

HCID 21952018(4-Phenoxyphenyl)-(7-iodoquinolin-4-yl)amine

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
120 °C

実験手順

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%) δH [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).

後処理

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

出典と根拠

ORDレコード
ord-ff57ce611b9046aabc723cc98a9f5ffc
出典データセット
uspto-grants-2004_03
特許番号
US06713485B2

関連ノート

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