Hydrochloric Acid → 7-METHOXY-QUINOXALIN-5-YLAMINE

HRID 428549ノート

反応式

HRID 428549 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([NH2:12])=[C:5]([N+:13]([O-])=O)[CH:4]=1.[CH:16]([CH:18]=O)=O.Cl.CCOC(C)=O>CCO.O.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6]([N:12]=[CH:16][CH:18]=[N:9]2)=[C:5]([NH2:13])[CH:4]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 7860GlyoxalHCID 8857Ethyl AcetateHCID 138470p-Anisidine, 2,6-dinitro-

生成物 1

HCID 3438617-METHOXY-QUINOXALIN-5-YLAMINE

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

A solution of 4-methoxy-2,6-dinitro-phenylamine (5 g, 23.5 mmol) in EtOH (200 mL) was hydrogenated over 10% Pd/C (2 g) at 40 psi for 1 hour. After H2 uptake had ceased, the reaction was filtered through a pad of celite and washed with EtOAc (50 mL) and concentrated. Glyoxal (8 ml, 704 mmol) and EtOH (50 mL) were immediately added and the reaction was heated at reflux for 2 hours. The cooled reaction was diluted with H2O (50 mL) and extracted into CH2Cl2 (3×100 mL). The organic phases were combined, dried over Na2SO4, filtered and concentrated. The resulting oil was purified by column chromatography (10% MeOH/CH2Cl2) affording 430 mg (10%) as a red oil. An analytical sample was prepared as the HCl salt from EtOAc affording a red solid.

後処理

  1. filtrationthe reaction was filtered through a pad of celite
  2. washwashed with EtOAc (50 mL)
  3. concentrationconcentrated
  4. temperaturethe reaction was heated
  5. temperatureat reflux for 2 hours
  6. customThe cooled reaction
  7. extractionextracted into CH2Cl2 (3×100 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting oil was purified by column chromatography (10% MeOH/CH2Cl2)
  12. customaffording 430 mg (10%) as a red oil

出典と根拠

ORDレコード
ord-5914a2c300ef4033ae31b003234e2a21
出典データセット
uspto-grants-2001_11
特許番号
US06313126B1

反応ノート

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