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Dimethylformamide → Tert-butyl 6-bromo-8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 2070123
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HRID 2070123 반응식
Cl.[NH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=[C:9]([Br:13])[CH:10]=2)[NH:5][C:4]1=[O:17].CN(C=O)C.C(N(CC)CC)C.[C:30](=O)([O:36]C(C)(C)C)[O:31][C:32]([CH3:35])([CH3:34])[CH3:33]>O>[Br:13][C:9]1[CH:10]=[C:11]2[C:6](=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=1)[NH:5][C:4](=[O:17])[CH:3]([NH:2][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:12]2
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 684113113-amino-6-bromo-8-nitro-3,4-dihydroquinolin-2(1H)-one hydrochloride

생성물 1

HCID 59620339Tert-butyl 6-bromo-8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate수율 92.3%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

3-Amino-6-bromo-8-nitro-3,4-dihydroquinolin-2(1H)-one hydrochloride (610 g) was added to N,N-dimethylformaldehyde (3 L), and triethylamine (554 mL) was added dropwise to the mixture under cooling on ice. Subsequently, di-tert-butyl carbonate (454 g) was added thereto, and the resultant mixture was stirred at room temperature for 30 minutes. Water (3 L) was added to the reaction mixture, and stirring was performed for 30 minutes under cooling on ice. The precipitates were recovered through filtration and washed sequentially with water and diisopropyl ether. The thus-obtained solid was dried, whereby the title compound (674 g) was yielded as a powdery compound.

후처리

  1. additionwas added dropwise to the mixture
  2. temperatureunder cooling on ice
  3. temperatureunder cooling on ice
  4. filtrationThe precipitates were recovered through filtration
  5. washwashed sequentially with water and diisopropyl ether
  6. customThe thus-obtained solid was dried

출처 및 근거

ORD 기록
ord-9f40415666314bb682ba8d96f2f1818f
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08299255B2

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