4-(2-Oxopropoxy)benzonitrile → 2-(4-Cyanophenoxy)-1-methylethylamine

HRID 2394311

反応式

HRID 2394311 の反応式
C([O-])(=O)C.[NH4+].C([BH3-])#[N:7].[Na+].[C:10]([C:12]1[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18](=O)[CH3:19])=[CH:14][CH:13]=1)#[N:11]>CO>[C:10]([C:12]1[CH:22]=[CH:21][C:15]([O:16][CH2:17][CH:18]([NH2:7])[CH3:19])=[CH:14][CH:13]=1)#[N:11]

参加物

5

反応物 3

HCID 3096034-(2-Oxopropoxy)benzonitrileHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 189727992-(4-Cyanophenoxy)-1-methylethylamine収率 27.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

293 g of ammonium acetate and 16.7 g of sodium cyanoborohydride were added to a solution containing 66.5 g of 4-cyanophenoxyacetone dissolved in 1500 ml of methanol, and the resultant mixture was stirred for 30 hours at room temperature. The reaction mixture was then concentrated under reduced pressure, and acidified with concentrated hydrochloric acid. 500 ml of diethyl ether and 300 ml of water were then added thereto. Subsequently, the resultant water layer was made basic with a 5% aqueous solution of sodium hydroxide, the solution was extracted with 1000 ml of diethyl ether, and then washed with water. The organic layer was then dried over anhydrous sodium sulfate, and the diethyl ether was removed under reduced pressure. The obtained residue was distilled under reduced pressure to yield 13.0 g of the desired product (19%). Boiling point: 132° C./0.26 mmHg.

後処理

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. addition500 ml of diethyl ether and 300 ml of water were then added
  3. extractionthe solution was extracted with 1000 ml of diethyl ether
  4. washwashed with water
  5. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  6. customthe diethyl ether was removed under reduced pressure
  7. distillationThe obtained residue was distilled under reduced pressure

出典と根拠

ORDレコード
ord-b9b37d453b7b4208a2c06b312704f361
出典データセット
uspto-grants-1998_09
特許番号
US05811424

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