홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Acetic Acid → methyl 6-(2,3-dihydro-1H-inden-2-ylamino)-2-methyl-4-phenylquinoline-3-carboxylate

HRID 570383
노트
인쇄 미리보기

반응식

HRID 570383 반응식
CC(O)=O.[NH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH3:16])[C:10]([C:17]([O:19][CH3:20])=[O:18])=[C:9]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][C:28]1=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH:28]1[NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH3:16])[C:10]([C:17]([O:19][CH3:20])=[O:18])=[C:9]2[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 119832-IndanoneHCID 5049666Sodium triacetoxyborohydrideHCID 68293887Methyl 6-amino-2-methyl-4-phenylquinoline-3-carboxylate

생성물 1

HCID 68294847methyl 6-(2,3-dihydro-1H-inden-2-ylamino)-2-methyl-4-phenylquinoline-3-carboxylate수율 72.5%

시약·촉매·용매 1

HCID 11
1,2-Dichloroethane
용매

실험 절차

A method of Abdel-Magid et al (J. Org. Chem., 61, 3849, 1996) was used: Glacial AcOH (0.2 ml) was added to a solution of the product of Step 2 (0.91 g, 3.31 mmol), 1H-inden-2(3H)-one (0.41 g, 3.31 mmol) and NaBH(OAc)3 (1.05 g, 4.9 mmol) in anhydrous 1,2-dichloroethane (12.5 ml). The resulting mixture was stirred overnight at room temperature under N2 than quenched by addition of 1N NaOH aq (1 ml). This was diluted to 60 ml with Et2O and washed with N2. The organic phase was dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography (SiO2, CH2Cl2) to give pure product as a yellow solid (0.98 g, 72%). 1H NMR (300 MHz, CDCl3) δ 7.84 (d, J=9.0 Hz, 1H), 7.34-7.49(m, 5H), 7.15-7.18(m, 4H), 7.07(dd, J=1.7, 9.0 Hz, 1H), 6.49(d, J=1.7 Hz, 1H), 4.11-4.18(m, 2H), 3.55(s, 3H), 3.2(dd, J=6.2, 16 Hz, 2H), 2.8(dd, J=6.2, 16 Hz, 2H), 2.68(s, 3H).

후처리

  1. customthan quenched by addition of 1N NaOH aq (1 ml)
  2. additionThis was diluted to 60 ml with Et2O
  3. washwashed with N2
  4. dry with materialThe organic phase was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customfiltrate evaporated to dryness under reduced pressure
  7. customThe residue was purified by flash column chromatography (SiO2, CH2Cl2)

출처 및 근거

ORD 기록
ord-445724af04a74dabb370ba3c8395e1f8
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09023848B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트