Sodium Sulfite → HCID 59409002, 화합물

HRID 1894731노트

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HRID 1894731 반응식
[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH2:2]1.[Br:13]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.O.C(OCC)(=O)C>[Br:13][C:9]1[CH:8]=[C:7]2[C:12]3=[C:11]([CH2:1][CH2:2][N:3]3[CH2:4][CH2:5][CH2:6]2)[CH:10]=1

참가 물질

7

반응물 3

HCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 120264Lilolidine

생성물 1

HCID 59409002HCID 59409002, 화합물수율 86.7%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline (4.0 g, 25.2 mmol) in N,N-dimethylformamide (160 ml) cooled to −30° C. was treated with a solution of N-bromosuccinimide (4.5 g, 25.3 mmol) in N,N-dimethylformamide (30 ml) dropwise over 5 minutes. The mixture was stirred for a further 15 minutes then treated with 10% aqueous sodium sulfite (100 ml) then diluted with water (500 ml) and ethyl acetate (300 ml). The aqueous layer was removed and the organic layer was washed with saturated aqueous sodium bicarbonate (100 ml), then water (3×150 ml). The organic layer was dried with anhydrous sodium sulfate and evaporated to dryness to give 8-bromo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline as a pale brown oil (5.2 g) which was used without further purification. 400 MHz 1H NMR (CDCl3) δ: 7.02 (m, 1H), 6.94 (m, 1H), 3.25 (t, 2H), 2.95 (m, 2H), 2.89 (t, 2H), 2.65 (t, 2H), 2.06 (m, 2H); LCMS: 238 and 240 [M+H].

후처리

  1. customThe aqueous layer was removed
  2. washthe organic layer was washed with saturated aqueous sodium bicarbonate (100 ml)
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-6e17d5abfb774c40a56d23ac148fa066
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513292B2

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