Water → 4-{4-[(4-Aminoanilino)carbonyl]anilino}-1-methylpyridinium chloride

HRID 547525노트

반응식

HRID 547525 반응식
[Cl-:1].[CH3:2][N+:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)=[O:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.O>CCO.[Fe]>[Cl-:1].[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:16]([C:13]2[CH:14]=[CH:15][C:10]([NH:9][C:6]3[CH:5]=[CH:4][N+:3]([CH3:2])=[CH:8][CH:7]=3)=[CH:11][CH:12]=2)=[O:17])=[CH:20][CH:21]=1

참가 물질

5

반응물 2

HCID 962WaterHCID 671999221-Methyl-4-{4-[(4-nitroanilino)carbonyl]anilino}pyridinium chloride

생성물 1

HCID 672001654-{4-[(4-Aminoanilino)carbonyl]anilino}-1-methylpyridinium chloride수율 80%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

Compound D4 (295 mg, 0.77 mmol) was dissolved in ˜5:1 EtOH:H2O (12 mL), and Fe dust (209 mg)was added. The mixture was vigorously stirred and refluxed for 4 h, and then filtered hot through a pad of Celite. The Celite was washed with boiling EtOH, and EtOH fractions were combined and evaporated to dryness. The residue was extracted into hot water, and filtered through Celite, and then evaporated to dryness. The residue was azeotroped with MeOH (3×20 mL), and then dissolved in MeOH (10 mL). Methanolic HCl (1.25 M, 5 mL) was added, and the solution stirred for 10 min. Solvent was removed under reduced pressure, and the residue was crystallized from MeOH/EtOAc to give D5 (218 mg, 80%); mp (MeOH/EtOAc); 1H NMR [(CD3)2SO] δ11.13 (s, 1 H, NH), 10.44 (s, 1 H, NH), 9.88 (br, 2 H, NH2), 8.36 (d, J=7.5 Hz, 2 H, ArH), 8.12 (d, J=8.6 Hz, 2 H, ArH), 7.86 (d, J=8.8 Hz, 2 H, ArH), 7.50 (d, J=8.8 Hz, 2 H, ArH), 7.32 (d, J=8.6 Hz, 2 H, ArH), 7.32 (d, J=7.5 Hz, 2 H, ArH), 7.30 (d, J=8.7 Hz, 2 H, ArH), 4.00 (s, 3 H, N+CH3); LCMS 319+ve

후처리

  1. temperaturerefluxed for 4 h
  2. filtrationfiltered hot through a pad of Celite
  3. washThe Celite was washed with boiling EtOH, and EtOH fractions
  4. customevaporated to dryness
  5. extractionThe residue was extracted into hot water
  6. filtrationfiltered through Celite
  7. customevaporated to dryness
  8. customThe residue was azeotroped with MeOH (3×20 mL)
  9. dissolutiondissolved in MeOH (10 mL)
  10. additionMethanolic HCl (1.25 M, 5 mL) was added
  11. stirringthe solution stirred for 10 min
  12. customSolvent was removed under reduced pressure
  13. customthe residue was crystallized from MeOH/EtOAc

출처 및 근거

ORD 기록
ord-db443d1f8c8d41b48c6961d11a41c949
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939546B2

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