4-Chloro-N-methylbenzenamine → N-(4-Chlorophenyl)-N-methyl-3-nitropyridin-2-amine

HRID 255694

反応式

HRID 255694 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1>Cl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([N:6]([CH3:7])[C:11]2[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 702724-Chloro-N-methylbenzenamineHCID 796132-Chloro-3-nitropyridine

生成物 1

HCID 13560173N-(4-Chlorophenyl)-N-methyl-3-nitropyridin-2-amine

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

To 90 g (0.63 mole) of 4-chloro-N-methylaniline heated to 115°-120° C. under nitrogen atmosphere with stirring was added 66.3 g (0.42 mole) of 2-chloro-3-nitropyridine in four portions over a period of 80 minutes. After stirring the reaction mixture for an additional 20 minutes at 115°-120° C., the temperature was increased to 135°-140° C. for an additional 20 minute period. The hot melt was poured into 700 ml of 2N hydrochloric acid solution. Red precipitate weighing 96 g was collected and dissolved in hot acetic acid and converted to the hydrochloride salt by adding etheral hydrogen chloride. The yield of the yellow solid was 90 g (72%). A portion of the salt was recrystallized from ethyl acetate-ethyl alcohol. On drying at 80° C. in vacuo, the hydrochloride salt dissociated to the free base, the title compound, m.p. 107°-110° C.

後処理

  1. stirringAfter stirring the reaction mixture for an additional 20 minutes at 115°-120° C.
  2. temperaturethe temperature was increased to 135°-140° C. for an additional 20 minute period
  3. customwas collected
  4. dissolutiondissolved in hot acetic acid
  5. additionby adding etheral hydrogen chloride
  6. customA portion of the salt was recrystallized from ethyl acetate-ethyl alcohol
  7. customOn drying at 80° C. in vacuo

出典と根拠

ORDレコード
ord-4adf197d5c0e4897aad2b22961966b79
出典データセット
uspto-grants-1987_10
特許番号
US04698430

関連ノート

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