Water → 1-(4-Aminophenyl)cyclohexanecarbonitrile

HRID 1477473ノート

反応式

HRID 1477473 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.O.[NH4+].[Cl-]>CCO.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:8][CH:9]=1

参加物

6

反応物 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 589937681-(4-Nitro-phenyl)-cyclohexanecarbonitrile

生成物 1

HCID 498745261-(4-Aminophenyl)cyclohexanecarbonitrile収率 100%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

A solution of 1-(4-nitro-phenyl)-cyclohexanecarbonitrile (0.500 g, 2.17 mmol, as prepared in the previous step) in EtOH (6 mL) and water (6 mL) was treated with NH4Cl (1.16 g, 21.7 mmol) and Fe powder (606 mg, 10.9 mmol) and heated to 50° C. for 2 h. The cooled mixture was filtered through Celite, and the filter cake was washed with MeOH. The solvents were evaporated in vacuo. The residue was partitioned between water (50 mL) and EtOAc (75 mL), and the layers were separated. The organic layer was dried over MgSO4 and concentrated in vacuo to afford the title compound (488 mg, 100%) as an orange oil. The compound was used in the following step without purification. Mass spectrum (ESI, m/z): Calcd. for C13H16N2, 201.1 (M+H). found 201.3.

後処理

  1. filtrationThe cooled mixture was filtered through Celite
  2. washthe filter cake was washed with MeOH
  3. customThe solvents were evaporated in vacuo
  4. customThe residue was partitioned between water (50 mL) and EtOAc (75 mL)
  5. customthe layers were separated
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-20666edda94a4b129cbd529b081e45d5
出典データセット
uspto-grants-2016_08
特許番号
US09403804B2

反応ノート

読み込み中…