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

HRID 13772

반응식

HRID 13772 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d685328ebf2549899ea59d9ce7212bdc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728131B2

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