2(1H)-Quinoxalinone → 7-bromo-1H-quinoxalin-2-one

HRID 751277

반응식

HRID 751277 반응식
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]1=[O:11].[Br:12]Br>C(O)(=O)C>[Br:12][C:8]1[CH:9]=[C:10]2[C:5]([N:4]=[CH:3][C:2](=[O:11])[NH:1]2)=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 145262(1H)-QuinoxalinoneHCID 24408Bromine

생성물 1

HCID 49132647-bromo-1H-quinoxalin-2-one

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Heat benzene-1,2-diamine (7.5 g, 69 mmol) and oxo-acetic acid ethyl ester (20 mL) in ethanol (100 mL) at 120° C. for 18 h. Cool, filter the resulting precipitate, and wash with dry ether to give 1H-quinoxalin-2-one (6.7 g). Dissolve 1H-quinoxalin-2-one in acetic acid (300 mL), add bromine (5 mL), and stir the reaction mixture for 1 h. Filter the resulting crystals and wash with ether to afford 7-bromo-1H-quinoxalin-2-one (7.2 g). Reflux 7-bromo-1H-quinoxalin-2-one in POCl3 (30 mL) for 18 h. Remove POCl3 in vacuo, dissolve the product in 3:1 chloroform/isopropyl alcohol, and wash the organic phase with saturated sodium bicarbonate. Dry over sodium sulfate and purify by silica gel flash chromatography eluting with dichloromethane to 10% methanol/90% dichloromethane to afford the title compound as a yellow solid (4.5 g, 58%). MS (electrospray, m/z) 243.0 and 245.0 (M+1).

후처리

  1. filtrationFilter the resulting crystals
  2. washwash with ether

출처 및 근거

ORD 기록
ord-2c4fe477a72147fe8cc62af5e65e81f6
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405299B2

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