Triethylamine → Tert-butyl 2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethylcarbamate

HRID 32373

반응식

HRID 32373 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[NH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32]>C(Cl)Cl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 12106198tert-Butyl [2-(2-aminoethoxy)ethyl]carbamate

생성물 1

HCID 12106199Tert-butyl 2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethylcarbamate수율 76.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A stirred solution of 4-chloro-3-nitroquinoline (31.4 g, 0.151 mol) in 500 mL of anhydrous CH2Cl2, under N2, was treated with triethylamine (43 mL, 0.308 mol) and tert-butyl 2-(2-aminoethoxy)ethylcarbamate (0.151 mol). After stirring overnight, the reaction mixture was washed with H2O (2×300 mL) and brine (300 mL). The organic portion was dried over Na2SO4 and concentrated to give a bright yellow solid. Recrystallization from ethyl acetate/hexanes gave 43.6 g of tert-butyl 2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethylcarbamate as bright yellow crystals.

후처리

  1. washthe reaction mixture was washed with H2O (2×300 mL) and brine (300 mL)
  2. dry with materialThe organic portion was dried over Na2SO4
  3. concentrationconcentrated
  4. customto give a bright yellow solid
  5. customRecrystallization from ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-d4f14702dfff4bce863601c6a4dcbddb
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427629B2

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