반응 #64903

반응 방정식

Phosphorous oxychloride

sodium hydroxide

5-aminoacenaphthene

sodium nitromalondialdehyde monohydrate

aniline hydrochloride

→

8-Nitro-10-azaacephenanthrene

용매

acetic acid

반응 조건

후처리

1. 1
   workup.STIRRINGThis mixture was stirred for 10 min
2. 2
   온도heated
3. 3
   온도at reflux for 2 h
4. 4
   온도heating
5. 5
   workup.WAITwas continued for 3 h
6. 6
   온도The resulting mixture was cooled to room temperature
7. 7
   추출extracted with dichloromethane
8. 8
   건조The extracts were dried over sodium sulfate and condensed to dryness
9. 9
   기타The condensed product was purified
10. 10
    기타to obtain a fluffy, bright yellow solid, 3.20 g (43%)

실험 절차

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).

출처