Methyl 3,5-dibromo-4-{(1Z)-3-[(2,6-dichlorophenyl)amino]-3-oxoprop-1-enyl}benzoate → Methyl 5-bromo-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

HRID 394209

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HRID 394209 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10](Br)[C:11]=1/[CH:12]=[CH:13]\[C:14]([NH:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24])=[O:15])[C:5]([O:7][CH3:8])=[O:6]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[C:10]2[C:11]=1[CH:12]=[CH:13][C:14](=[O:15])[N:16]2[C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24]

참가 물질

3

반응물 1

HCID 69919937Methyl 3,5-dibromo-4-{(1Z)-3-[(2,6-dichlorophenyl)amino]-3-oxoprop-1-enyl}benzoate

생성물 1

HCID 22648178Methyl 5-bromo-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

Methyl 3,5-dibromo-4-{(1Z)-3-[(2,6-dichlorophenyl)amino]-3-oxoprop-1-enyl}benzoate (1.25 g)(contaminated with 20% of the E isomer) was dissolved in dimethylformamide(36 mL) and the solution degassed with argon. Copper (I) iodide (340 mg) and dry potassium carbonate (468 mg) were added and the mixture heated to 80° C. for 30 min. The reaction mixture was poured into 5% ammonium hydroxide solution and extracted into ethyl acetate, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography eluting with 80% hexane: 20% ethyl acetate to give the title compound.

후처리

  1. customthe solution degassed with argon
  2. additionCopper (I) iodide (340 mg) and dry potassium carbonate (468 mg) were added
  3. additionThe reaction mixture was poured into 5% ammonium hydroxide solution
  4. extractionextracted into ethyl acetate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 80% hexane

출처 및 근거

ORD 기록
ord-50f029a29e7c40aa80bf4bac3d5fbc1b
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809199B2

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