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

HRID 1403746

反応式

HRID 1403746 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%) 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).

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-a33eb3d5ed5d453989108329cbdd1d3a
出典データセット
uspto-grants-2014_12
特許番号
US08912205B2

関連ノート

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