8-Aminoquinoline → 5-bromoquinolin-8-amine

HRID 2090052노트

반응식

HRID 2090052 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Br:12]N1C(=O)CCC1=O>CC#N>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:12])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

참가 물질

4

반응물 2

HCID 113598-AminoquinolineHCID 67184N-bromobutanimide2회

생성물 1

HCID 6138295-bromoquinolin-8-amine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 8-aminoquinoline (4.0 g, 28 mmol) in CH3CN (185 mL) was added N-bromosuccinimide (2.47 g, 13.9 mmol). After stirring for 15 minutes, a second portion of N-bromosuccinimide (2.71 g, 15.2 mmol) was added. After stirring for an additional 30 minutes, the mixture was concentrated. The residue was dissolved in EtOAc, then washed with water (2×100 mL) and saturated NaCl (aq) (100 mL). The organics were dried over Na2SO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 10-15% EtOAc/hexanes to afford the title compound as a white solid: 1H NMR (500 MHz, CDCl3): δ 8.79 (dd, J=1.5, 4.1 Hz, 1H), 8.46 (dd, J=1.5, 8.5 Hz, 1H), 7.60 (d, J=8.1 Hz, 1H), 7.52 (dd, J=4.1, 8.5 Hz, 1H), 6.83 (d, J=8.1 Hz, 1H); LC7: 2.48 min. (M+H) 225.

후처리

  1. stirringAfter stirring for an additional 30 minutes
  2. concentrationthe mixture was concentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water (2×100 mL) and saturated NaCl (aq) (100 mL)
  5. dry with materialThe organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 10-15% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-dcd643c531cc404aa4c7b0e30ce93188
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436015B2

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