2-Methyl-5-Nitroaniline → 2-[(4-Chloro)pyridin-2-ylamino]-1-methyl-4-nitrobenzene

HRID 13772

反応式

HRID 13772 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:11]=1[NH2:12].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:12][C:11]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:10]=2[CH3:9])[CH:7]=1

参加物

7

反応物 4

HCID 74442-Methyl-5-NitroanilineHCID 10796Cesium carbonateHCID 335152,4-DichloropyridineHCID 634876Binap, (A+-)-

生成物 1

HCID 686937452-[(4-Chloro)pyridin-2-ylamino]-1-methyl-4-nitrobenzene収率 34.2%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

To 2.00 g of 2,4-dichloropyridine, 2.26 g of 2-methyl-5-nitroaniline, 121 mg of palladium (II) acetate, 336 mg of (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl [(±)-BINAP] and 6.16 g of cesium carbonate, 120 ml of toluene was added, and then the mixture was stirred with heating at 70° C. for 23 hours under an argon atmosphere. After insolubles were removed by filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain a crude product. The crude product was washed with diethyl ether to obtain 1.22 g of the objective compound as yellow crystals.

後処理

  1. customAfter insolubles were removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel column chromatography
  4. customto obtain a crude product
  5. washThe crude product was washed with diethyl ether

出典と根拠

ORDレコード
ord-d685328ebf2549899ea59d9ce7212bdc
出典データセット
uspto-grants-2010_06
特許番号
US07728131B2

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