Hydrochloric Acid → 2-Amino-6-nitrobenzonitrile

HRID 471600노트

반응식

HRID 471600 반응식
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[C:6]=1[C:7]#[N:8])([O-:4])=[O:3].CCOC(C)=O.O>CO.O1CCOCC1.[Fe]>[NH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:5]([N+:2]([O-:4])=[O:3])[C:6]=1[C:7]#[N:8]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 520718Dinitrobenzonitrile

생성물 1

HCID 127157292-Amino-6-nitrobenzonitrile수율 68.1%

시약·촉매·용매 3

HCID 23925Iron촉매2회HCID 887Methanol용매HCID 312751,4-Dioxane용매

반응 조건

온도
70 °C

실험 절차

Concentrated HCl (39 mL) was added to a solution of 2,6-dinitrobenzonitrile (11.3 g, 58.5 mmol) in MeOH (235 mL) and 1,4-dioxane (145 mL) at 70° C. External heating was removed, and iron powder (11.44 g, 205 mmol) was added slowly in portions at a rate which maintained a temperature of 70° C. After the addition of iron was complete, the reaction was heated at reflux for a further 30 min, then cooled to room temperature and poured into EtOAc (400 mL) and water (400 mL). The solids were filtered out and extracted twice with boiling EtOAc (300 mL). The combined organic extract was dried with MgSO4, filtered and evaporated to give 2-amino-6-nitrobenzonitrile (6.5 g, 68%) as a red solid, which was used without further purification. 1H-NMR (400 MHz, DMSO-d6) δ 7.48-7.54 (m, 1H), 7.41-7.45 (m, 1H), 7.18-7.22 (m, 1H), 6.74 (broad s, 2H).

후처리

  1. temperatureExternal heating
  2. customwas removed
  3. temperaturethe reaction was heated
  4. temperatureat reflux for a further 30 min
  5. temperaturecooled to room temperature
  6. filtrationThe solids were filtered out
  7. extractionextracted twice with boiling EtOAc (300 mL)
  8. extractionThe combined organic extract
  9. dry with materialwas dried with MgSO4
  10. filtrationfiltered
  11. customevaporated

출처 및 근거

ORD 기록
ord-0609f4aa410144d587d59fd804bdcd6a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633186B2

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