Hydrochloric Acid → 2-Amino-6-nitrobenzonitrile

HRID 711737ノート

反応式

HRID 711737 の反応式
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]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 520718Dinitrobenzonitrile

生成物 1

HCID 127157292-Amino-6-nitrobenzonitrile収率 68.1%

試薬・触媒・溶媒 3

HCID 23925Iron触媒2 回HCID 887Methanol溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a83bd4e77f7343d4a6cd3f8be6790e57
出典データセット
uspto-grants-2015_11
特許番号
US09181276B2

反応ノート

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