2-(4-Chlorophenoxy)benzonitrile → (2-(4-chlorophenoxy)phenyl)MethanaMine

HRID 1642243ノート

反応式

HRID 1642243 の反応式
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9][NH2:10])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 141307012-(4-Chlorophenoxy)benzonitrileHCID 21226445Aluminium lithium hydride

生成物 1

HCID 19926667(2-(4-chlorophenoxy)phenyl)MethanaMine収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

AMR01073 To an ice cooled solution of 2-(4-chlorophenoxy)benzonitrile (AMR01071, 200 mg, 8.75 mmol) in dry THF (10 mL) was added a solution of LiAlH4 (THF 1M, 1.75 mL) under nitrogen. After stirring at room temperature for 3 h, the reaction mixture was cooled again and quenched with the minimum amount of saturated NH4Cl solution. The insoluble material was removed by filtration, and washed with DCM. The filtrate was dried (MgSO4) and the solvent evaporated to give 2-(4-chlorophenoxy)benzylamine (AMR01073, 203 mg, 100%) as an oil, which was used in the next step without further purification. AMR01076 Following the same procedure, from AMR01071 (1.5 g, 6.53 mmol) and LiAlH4 solution (THF 1M, 13 mL) in dry THF (30 mL), 2-(4-chlorophenoxy)benzylamine (AMR0106, 1.38 g, 90%) was obtained as an oil. Rf: 0.35 (DCM/MeOH 9:1) 1H NMR (270 MHz, CDCl3) δ 1.42 (2H, br s, NH2), 3.84 (2H, s, CH2), 6.84-6.90 (3H, m, ArH), 7.13 (1H, m, ArH), 7.21 (1H, dd, J=7.6, 2.0 Hz, ArH), 7.26 (2H, AA′BB′, ArH) and 7.38 (1H, td, J=7.4, 1.7 Hz, ArH). LC/MS (APCI) tr=1.40 min, m/z 236.38 (34), 234.36 (M++H, 100), 217.29 (M+—NH3, 35).

後処理

  1. temperaturethe reaction mixture was cooled again
  2. customquenched with the minimum amount of saturated NH4Cl solution
  3. customThe insoluble material was removed by filtration
  4. washwashed with DCM
  5. dry with materialThe filtrate was dried (MgSO4)
  6. customthe solvent evaporated

出典と根拠

ORDレコード
ord-d41f9b97315049689732e620ee75855c
出典データセット
uspto-grants-2012_02
特許番号
US08119627B2

反応ノート

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