2-Methyl-4-nitrophenol → 4-(2-Methyl-4-nitrophenoxy)pyridin-2-amine

HRID 492687

反応式

HRID 492687 の反応式
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[CH3:19].C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[CH3:19][C:11]1[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=1[O:9][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=1

参加物

5

反応物 3

HCID 74422-Methyl-4-nitrophenolHCID 81531DiisopropylethylamineHCID 5818662-Amino-4-chloropyridine

生成物 1

HCID 231530654-(2-Methyl-4-nitrophenoxy)pyridin-2-amine収率 45.7%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
150 °C

実験手順

2-Amino-4-chloropyridine (5.0 g), N-methyl pyrrolidone (40 ml), 2-hydroxy-5-nitrotoluene (11.9 g) and diisopropylethylamine (20.1 g) were put in a reaction vessel, followed by heating and stirring under a nitrogen atmosphere at 150° C. for 5 days. The reaction mixture was cooled down to room temperature and concentrated under a reduced pressure. To the resultant residue was added a saturated aqueous solution of sodium hydrogencarbonate, followed by stirring at room temperature overnight. To the reaction mixture was added tetrahydrofuran (200 ml) to partition. The aqueous layer was extracted with diethyl ether (100 ml). The organic layer was washed with brine (100 ml×2), dried over anhydrous sodium sulfate, and concentrated under a reduced pressure. The precipitated solid was suspended in diethyl ether and filtered off. The solid was washed with diethyl ether:ethyl acetate=1:1, and dried under aeration to provide the titled compound (4.36 g, 45.7%) as a yellow solid.

後処理

  1. temperatureby heating
  2. temperatureThe reaction mixture was cooled down to room temperature
  3. concentrationconcentrated under a reduced pressure
  4. additionTo the resultant residue was added a saturated aqueous solution of sodium hydrogencarbonate
  5. stirringby stirring at room temperature overnight
  6. additionTo the reaction mixture was added tetrahydrofuran (200 ml)
  7. customto partition
  8. extractionThe aqueous layer was extracted with diethyl ether (100 ml)
  9. washThe organic layer was washed with brine (100 ml×2)
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under a reduced pressure
  12. filtrationfiltered off
  13. washThe solid was washed with diethyl ether
  14. dry with materialethyl acetate=1:1, and dried under aeration

出典と根拠

ORDレコード
ord-256b1919a3cd490aad263a9702caff63
出典データセット
uspto-grants-2009_05
特許番号
US07531532B2

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