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

HRID 1603849ノート

反応式

HRID 1603849 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 22504935Water 2-methoxyethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-059b58db1bc043a792c17ae3054ad7e7
出典データセット
uspto-grants-1999_11
特許番号
US05990146

反応ノート

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