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Sulfamic Acid → Methyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylate

HRID 570381
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HRID 570381 반응식
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.NS(O)(=O)=O.[C:24]([O:30][CH3:31])(=[O:29])[CH2:25][C:26]([CH3:28])=O>CCOC(C)=O>[CH3:28][C:26]1[C:25]([C:24]([O:30][CH3:31])=[O:29])=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]2[C:2](=[CH:15][CH:14]=[C:13]([N+:16]([O-:18])=[O:17])[CH:12]=2)[N:1]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 5987Sulfamic AcidHCID 7757Methyl acetoacetateHCID 156812-Amino-5-nitrobenzophenone

생성물 1

HCID 26609017Methyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylate수율 80%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

A mixture of 2-amino-5-nitrobenzophenone (1 g, 4.1 mmol), H2NSO3H (0.04 g, 041 mmol) and methyl acetoacetate (1.11 ml, 10.3 mmol) was stirred overnight at 120° C. under N2, than cooled to room temperature, diluted to 100 ml with EtOAc and washed with H2O. The organic phase was dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by crystallization from EtOH to give pure product as a creamy solid (1.05 g, 80%). 1H NMR (300 MHz, CDCl3) δ 8.52 (d, J=2.5 Hz, 1H), 8.48 (dd, J=2.5, 9.2 Hz, 1H), 7.53(m, 3H), 7.34(m, 2H), 3.59(s, 3H), 2.8(s, 3H).

후처리

  1. temperaturethan cooled to room temperature
  2. washwashed with H2O
  3. dry with materialThe organic phase was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customfiltrate evaporated to dryness under reduced pressure
  6. customThe residue was purified by crystallization from EtOH

출처 및 근거

ORD 기록
ord-2057103ac4fa44a582aa7092f6b7487c
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09023848B2

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