3-Nitroaniline → 3-chloro-N-(3-nitrophenyl)propanamide

HRID 716854노트

반응식

HRID 716854 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[Cl:11][CH2:12][CH2:13][C:14](Cl)=[O:15]>C1COCC1>[Cl:11][CH2:12][CH2:13][C:14]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:15]

참가 물질

4

반응물 2

HCID 74233-NitroanilineHCID 693643-Chloropropionyl chloride

생성물 1

HCID 34652363-chloro-N-(3-nitrophenyl)propanamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

To a stirred solution of 3-nitroaniline (37a, 6.9 g, 50 mmol) in THF (50 mL) was added dropwise 3-chloropropionyl chloride (10 mL, 100 mmol) over 30 min under argon atmosphere. The reaction was stirred at 50° C. for 10 h. After cooling, the reaction mixture was evaporated to dryness under vacuo and the residue was neutralized with saturated aqueous solution of NaHCO3 and the solid product was collected by filtration, washed with water followed by hexane, and dried to afford 3-chloro-N-(3-nitrophenyl)propanamide, 10.61 g (92%), mp 86-88° C. (Lit. 100-102° C.57). 1H NMR (DMSO-d6) δ: 2.87-2.90 (2H, t, J=9.9 Hz, CH2), 3.90-3.92 (2H, t, J=9.9 Hz, CH2), 7.61-7.64 (1H, t, J=6.6 and 6.6 Hz, Ar—H), 7.90-7.94 (2H, m, Ar—H), 8.65-8.66 (1H, t, J=3.4 and 1.7 Hz, Ar—H), 10.59 (1H, brs, NH).

후처리

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated to dryness under vacuo
  3. filtrationthe solid product was collected by filtration
  4. washwashed with water
  5. customdried

출처 및 근거

ORD 기록
ord-62019b26578c45fa93f418931b53bffc
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193687B2

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