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

HRID 492687

Reaction equation

HRID 492687 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-256b1919a3cd490aad263a9702caff63
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Linked notes

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