Benzenamine hydrochloride (1:1) → 8-Nitro-10-azaacephenanthrene

HRID 36625

反応式

HRID 36625 の反応式
[NH2:1][C:2]1[C:12]2[C:13]3[C:5]([CH2:6][CH2:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.[CH:14](/[O-])=[C:15](\[N+:18]([O-:20])=[O:19])/[CH:16]=O.O.[Na+].Cl.NC1C=CC=CC=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>C(O)(=O)C>[N+:18]([C:15]1[CH:14]=[C:3]2[C:2](=[N:1][CH:16]=1)[C:12]1=[C:13]3[C:5]([CH2:6][CH2:7][C:8]3=[CH:9][CH:10]=[CH:11]1)=[CH:4]2)([O-:20])=[O:19]

参加物

7

反応物 5

HCID 8870Benzenamine hydrochloride (1:1)HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 625475-AminoacenaphtheneHCID 12244252sodium N-oxido-1,3-dioxopropanimine oxide hydrate

生成物 1

HCID 233640248-Nitro-10-azaacephenanthrene

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 5-aminoacenaphthene (Grabe, C. Liebigs Ann. der Chemie 1903, 327, 77) (5.0 g, 29.5 mmol) and sodium nitromalondialdehyde monohydrate (Fanta, P. E. Org. Syntheses Coll. vol. 4 1963, 844) (5.51 g, 35 mmol) in acetic acid (140 mL) was stirred for 1 h at room temperature and aniline hydrochloride (5.21 g, 40.2 mmol) was added. This mixture was stirred for 10 min and heated at reflux for 2 h. Phosphorous oxychloride (3 mL, 32.2 mmol) was added and heating was continued for 3 h. The resulting mixture was cooled to room temperature and poured into ice/water (200 mL). The aqueous mixture was neutralized with 2M sodium hydroxide solution and extracted with dichloromethane. The extracts were dried over sodium sulfate and condensed to dryness. The condensed product was purified using flash chromatography (20% hexane/dichloromethane, silica gel) to obtain a fluffy, bright yellow solid, 3.20 g (43%): MS m/e 251 (M+H +); 1H NMR (CD2C12, 300 MHz) δ 3.48-3.55 (m, 4H), 7.56 (s, 1H), 7.68 (d, J=7.0 Hz, 1H), 7.77 (t, J=7.8 Hz, 1H), 8.79 (d, J=8.1 Hz, 1H), 8.94 (d, J=2.5 Hz, 1H), 9.65 (d, J=2.5 Hz, 1H).

後処理

  1. stirringThis mixture was stirred for 10 min
  2. temperatureheated
  3. temperatureat reflux for 2 h
  4. temperatureheating
  5. waitwas continued for 3 h
  6. temperatureThe resulting mixture was cooled to room temperature
  7. extractionextracted with dichloromethane
  8. dry with materialThe extracts were dried over sodium sulfate and condensed to dryness
  9. customThe condensed product was purified
  10. customto obtain a fluffy, bright yellow solid, 3.20 g (43%)

出典と根拠

ORDレコード
ord-1e8427f94cd94078aa77583ff7c2032f
出典データセット
uspto-grants-1995_05
特許番号
US05416089

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