4-Pyridinecarboxylic acid, 1-oxide → N-(2-amino-4,5-dichlorophenyl)-4-pyridinecarboxamide-1-oxide

HRID 568405

反応式

HRID 568405 の反応式
[N+:1]1([O-:10])[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:23][C:24]1[CH:25]=[C:26]([NH2:32])[C:27]([NH2:31])=[CH:28][C:29]=1[Cl:30]>CN(C)C=O.ClCCl>[NH2:32][C:26]1[CH:25]=[C:24]([Cl:23])[C:29]([Cl:30])=[CH:28][C:27]=1[NH:31][C:7]([C:4]1[CH:3]=[CH:2][N+:1]([O-:10])=[CH:6][CH:5]=1)=[O:9]

参加物

6

反応物 3

HCID 261304-Pyridinecarboxylic acid, 1-oxideHCID 682631,1'-CarbonyldiimidazoleHCID 792974,5-Dichloro-1,2-phenylenediamine

生成物 1

HCID 135589633N-(2-amino-4,5-dichlorophenyl)-4-pyridinecarboxamide-1-oxide収率 16.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A suspension of 4-pyridinecarboxylic acid-1-oxide (2.84 g, 20.4 mmol) and 1,1'-carbonyldiimidazole (3.64 g, 22.4 mmol) in dry dimethylformamide (50 ml) was stirred for 4 hours under an air-lock and the resulting solution added dropwise over 1 hour to a stirred solution of 4,5-dichloro-1,2-benzenediamine (7.23 g, 40.8 mmol) in dichloromethane (50 ml) under air lock. After 2.5 days, the mixture was evaporated in vacuo and the residue purified by chromatography [SiO2 ; dichloromethane-methanoltriethylamine (100:3:1)]. Recrystallisation from ethanol-methanol gave the title compound (1.00 g), m.p. >300°. The compound exhibited infra-red spectral bands at 859, 1182, 1260, 1534, 1671, 3253, 3335 and 3417 cm-1. The NMR spectrum of the compound in DMSO-d6 exhibited the following signals: (δ in ppm from TMS) broad 2 proton signal at 5.5; 1 proton singlet at 6.97; 1 proton singlet at 7.42; 2 proton doublet (J7 Hz) at 7.96; 2 proton doublet (J7 Hz) at 8.37 and broad 1 proton singlet at 9.9.

後処理

  1. waitAfter 2.5 days
  2. customthe mixture was evaporated in vacuo
  3. customthe residue purified by chromatography [SiO2 ; dichloromethane-methanoltriethylamine (100:3:1)]
  4. customRecrystallisation from ethanol-methanol

出典と根拠

ORDレコード
ord-27154df1759e4805817993ae1e920add
出典データセット
uspto-grants-1988_03
特許番号
US04728658

関連ノート

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