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

HRID 1403746

반응식

HRID 1403746 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a33eb3d5ed5d453989108329cbdd1d3a
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912205B2

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