Water → Dimethyl{2-[(2-methyl-3-nitrophenyl)oxy]ethyl}amine

HRID 419322

反応式

HRID 419322 の反応式
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].Cl.Cl[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17].C([O-])([O-])=O.[K+].[K+].O>C(O)CCC>[CH3:17][N:16]([CH3:18])[CH2:15][CH2:14][O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[CH3:1]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 795792-Methyl-3-nitrophenolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

生成物 1

HCID 59452562Dimethyl{2-[(2-methyl-3-nitrophenyl)oxy]ethyl}amine収率 100%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
80 °C

実験手順

To a slurry containing 5.0 g (33 mmol) of 2-methyl-3-nitrophenol, 9.4 g (65.2 mmol) of (2-chloroethyl)dimethylamine hydrochloride, 9.0 g (65.3 mmol) of K2CO3, and 100 mL of H2O was added 100 mL of butanol and the reaction mixture was heated at 80° C. for 13 h. The reaction mixture was extracted with EtOAc and the combined organic layers were dried over MgSO4 and filtered. The solvents were removed under reduced pressure and the residue was subjected to silica gel chromatography to give 7.4 g (100%) of dimethyl{2-[(2-methyl-3-nitrophenyl)oxy]ethyl}amine as a brown oil. 1HNMR (400 MHz, DMSO-d6) δ 7.29-7.42 (m, 3H), 4.11 (t, J=5.6 Hz, 2H), 2.66 (t, J=5.6 Hz, 2H), 2.22 (s, 3H), 2.20 (s, 6H). MS (ESI+) m/z 225 [M+H].

後処理

  1. extractionThe reaction mixture was extracted with EtOAc
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customThe solvents were removed under reduced pressure

出典と根拠

ORDレコード
ord-82c8f6fcd51a4c0494a5b00260ed2a8f
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

関連ノート

読み込み中…