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

HRID 547525ノート

反応式

HRID 547525 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-db443d1f8c8d41b48c6961d11a41c949
出典データセット
uspto-grants-2011_05
特許番号
US07939546B2

反応ノート

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