Hydrochloric Acid → 3-nitro-N-phenylpyridin-4-amine

HRID 1603849

반응식

HRID 1603849 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>O.COCCO>[C:12]1([NH:11][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 27357814-Chloro-3-nitropyridine

생성물 1

HCID 6120053-nitro-N-phenylpyridin-4-amine

시약·촉매·용매 1

HCID 22504935Water 2-methoxyethanol용매

실험 절차

A solution of 4-chloro-3-nitropyridine (II: R'=4-aza, halogen=Cl) (3.22 g, 0.020 mol), aniline (III: R1' =H) (1.85 mL, 0.020 mol) and conc. HCl (0.17 mL, 0.02 mol) in 1:1 water/2-methoxyethanol (40 mL) was refluxed for 18 hours, then concentrated to dryness. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc, and the organic portion was worked up to give an oil which was chromatographed on silica gel. Petroleum ether eluted foreruns, while EtOAc/petroleum ether (1:1) gave 4-(N-phenylamino)-3-nitropyridine (VI: R'=4-aza, R1'=H) (2.02 g, 41%); mp (EtOAc/petroleum ether) 119° C.

후처리

  1. concentrationconcentrated to dryness
  2. customThe residue was partitioned between saturated aqueous NaHCO3 and EtOAc
  3. customto give an oil which
  4. customwas chromatographed on silica gel

출처 및 근거

ORD 기록
ord-059b58db1bc043a792c17ae3054ad7e7
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05990146

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