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

HRID 992070노트

반응식

HRID 992070 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 3438617-METHOXY-QUINOXALIN-5-YLAMINE

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d8ddaf26918b49049d04554af2c1677d
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06465482B2

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