9-Nitroanthracene → 9-Aminoanthracene

HRID 910707

반응식

HRID 910707 반응식
[Sn](Cl)(Cl)(Cl)Cl.[N+:6]([C:9]1[C:10]2[C:15]([CH:16]=[C:17]3[C:22]=1[CH:21]=[CH:20][CH:19]=[CH:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2)([O-])=O>Cl.C(O)(=O)C>[CH:21]1[C:22]2[C:17](=[CH:16][C:15]3[C:10]([C:9]=2[NH2:6])=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:18]=[CH:19][CH:20]=1

참가 물질

5

반응물 2

HCID 117679-NitroanthraceneHCID 24287Tin tetrachloride

생성물 1

HCID 130699-Aminoanthracene수율 74%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매

실험 절차

To a solution of tin chloride (25.4 g, 134 mmol) in concentrated hydrochloric acid (HCl, 210 mL) was added dropwise a solution of 9-nitroanthracene (10.0 g, 44.8 mmol) in acetic acid (420 mL), and the mixture was heated to reflux for 1 hour. The mixture was cooled to room temperature and filtered. The residue was treated with an aqueous solution of sodium hydroxide (NaOH, 1 N, 300 mL) and extracted with dichloromethane (CH2Cl2). The organic layer was dried over magnesium sulfate (MgSO4) and concentrated to give anthracen-9-yl-amine as brown crystals (6.41 g, 74% yield). 1H NMR (CDCl3) δ 8.00-7.95 (4H, m), 7.91 (1H, s), 7.47-7.42 (4H, m), 4.89 (2H, br-s).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. filtrationfiltered
  4. additionThe residue was treated with an aqueous solution of sodium hydroxide (NaOH, 1 N, 300 mL)
  5. extractionextracted with dichloromethane (CH2Cl2)
  6. dry with materialThe organic layer was dried over magnesium sulfate (MgSO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e696a92ca0974b32b90b15be19431dfb
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022214B2

연결된 노트

불러오는 중…