Diethyl Ether → 2-Amino-4-(4-amino-3-methoxyphenoxy)pyridine

HRID 492712ノート

反応式

HRID 492712 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH3:10].[H-].[Na+].[NH2:13][C:14]1[CH:19]=[C:18](Cl)[CH:17]=[CH:16][N:15]=1.C(OCC)C>CS(C)=O>[NH2:13][C:14]1[CH:19]=[C:18]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([O:9][CH3:10])[CH:4]=2)[CH:17]=[CH:16][N:15]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 5818662-Amino-4-chloropyridineHCID 198180564-Amino-3-methoxyphenol

生成物 1

HCID 231532722-Amino-4-(4-amino-3-methoxyphenoxy)pyridine収率 34%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

4-Amino-3-methoxyphenol (5.88 g) was dissolved in dimethyl sulfoxide (80 ml) while stirring, and then 60% sodium hydride (1.6 g) was added thereto gradually under a nitrogen stream, followed by stirring for 20 min. 2-amino-4-chloropyridine (2.75 g) was then added thereto, followed by stirring at 160° C. for 8 hrs. The reaction mixture was cooled down to room temperature, and partitioned between ethyl acetate and water. The organic layer was washed with water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate, then ethyl acetate:methanol=9:1). Fractions containing the target compound were concentrated to give a residue, to which diethyl ether was then added to precipitate crystals. The crystals were filtered and dried under aeration to provide the titled compound (1.56 g, 34%) as pale brown crystals.

後処理

  1. stirringby stirring for 20 min
  2. stirringby stirring at 160° C. for 8 hrs
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with water and brine in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under a reduced pressure
  7. customto give a residue, which
  8. customwas then purified by silica gel column chromatography (eluent
  9. additionFractions containing the target compound
  10. concentrationwere concentrated
  11. customto give a residue
  12. customto precipitate crystals
  13. filtrationThe crystals were filtered
  14. customdried under aeration

出典と根拠

ORDレコード
ord-ebac8427174d4ed4b392bc341c46ac19
出典データセット
uspto-grants-2009_05
特許番号
US07531532B2

反応ノート

読み込み中…