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

HRID 419322노트

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HRID 419322 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 2631-Butanol용매

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온도
80 °C

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-82c8f6fcd51a4c0494a5b00260ed2a8f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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