Methanol → (6-(Pyridin-2-yloxymethyl)-pyridin-3-yl)-acetohydroximoyl chloride

HRID 1691266ノート

反応式

HRID 1691266 の反応式
CO.[N+:3]([CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[N:12][CH:13]=1)([O-])=[O:4].C[O-].[Li+].C(Cl)[Cl:26]>[Ti](Cl)(Cl)(Cl)Cl.O>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][CH2:14][C:11]1[N:12]=[CH:13][C:8]([CH2:7][C:6]([Cl:26])=[N:3][OH:4])=[CH:9][CH:10]=1

参加物

7

反応物 4

HCID 887MethanolHCID 6344DichloromethaneHCID 4177230Lithium methanolateHCID 592554515-(2-Nitro-ethyl)-2-(pyridin-2-yloxymethyl)-pyridine

生成物 1

HCID 72262898(6-(Pyridin-2-yloxymethyl)-pyridin-3-yl)-acetohydroximoyl chloride

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒2 回HCID 962Water溶媒

実験手順

To a methanol (5 mL) solution of 5-(2-nitro-ethyl)-2-(pyridin-2-yloxymethyl)-pyridine (93 mg, 0.36 mmol) described in Manufacturing Example 154-1-7 was added lithium methoxide (27 mg, 0.72 mmol), which was stirred for 5 minutes at room temperature. The reaction mixture was concentrated under a reduced pressure. To a suspension of this residue in tetrahydrofuran (3 mL) and methylene chloride (3 mL) was added titanium (IV) tetrachloride (87 μL, 0.79 mmol) under nitrogen atmosphere at −78° C., which was stirred for 2 hours at 0° C. More titanium(IV) tetrachloride (50 μL, 0.46 mmol) was added at −78° C., which was stirred for 3 hours at 0° C. Water was added to the reaction mixture at 0° C., which was then extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (24 mg). This compound was used in the following reaction without any further purification.

後処理

  1. concentrationThe reaction mixture was concentrated under a reduced pressure
  2. additionTo a suspension of this residue in tetrahydrofuran (3 mL)
  3. stirringwhich was stirred for 2 hours at 0° C
  4. stirringwhich was stirred for 3 hours at 0° C
  5. extractionwhich was then extracted with ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under a reduced pressure

出典と根拠

ORDレコード
ord-02c0e7a148ad4c658214c1f328d9cd69
出典データセット
uspto-grants-2012_04
特許番号
US08153662B2

反応ノート

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