N-bromobutanimide → 4-(Bromomethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

HRID 25749

반응식

HRID 25749 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:20])([CH3:19])[CH:13]=[C:12]2[CH3:21].[Br:22]N1C(=O)CCC1=O>C(#N)C>[Br:22][CH2:21][C:12]1[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH:10]=2)[NH:15][C:14]([CH3:20])([CH3:19])[CH:13]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 225665156-(2-Methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

생성물 1

HCID 225665354-(Bromomethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline수율 75.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 800 mg of 6-(2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline and 90 mL of acetonitrile was treated with 510 mg of N-bromosuccinimide (NBS) at −20° C. for 2 minutes. The reaction was quenched with water and extracted with EtOAc three times. The organic layers were combined and washed with 10% aqueous sodium thiosulfate (Na2S2O3) solution, water, and brine and then dried over magnesium sulfate. The residue was purified by flash chromatography to yield 776 mg of 4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline as a solid.

후처리

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc three times
  3. washwashed with 10% aqueous sodium thiosulfate (Na2S2O3) solution, water, and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-9f361d9435e84122963f467ad2b130fc
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858627B2

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