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

HRID 570379
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HRID 570379 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][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:9]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH2:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][C:31]1=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH:31]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][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])=[C:9]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
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참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 119832-IndanoneHCID 5049666Sodium triacetoxyborohydride2회HCID 86713557tert-Butyl 6-amino-2-methyl-4-phenylquinoline-3-carboxylate

생성물 1

HCID 86713558tert-Butyl 6-(2,3-dihydro-1H-inden-2-ylamino)-2-methyl-4-phenylquinoline-3-carboxylate수율 71%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A method of Abdel-Magid et al (J. Org. Chem., 61, 3849, 1996) was used: Glacial AcOH (0.25 ml) was added to a solution of the product of Step 2 (1.46 g, 4.4 mmol), 1H-inden-2(3H)-one (0.46 g, 4.5 mmol) and NaBH(OAc)3 (1.4 g, 6.55 mmol) in anhydrous 1,2-dichloroethane (17 ml). The resulting mixture was stirred overnight at room temperature under N2 and to it more of NaBH(OAc)3 (0.4 g, 1.9 mmol) was added. After 2 h of stirring at room temperature, the mixture was quenched by addition of 1N NaOH aq (5 ml). This was diluted to 60 ml with Et2O and washed with H2O and brine. 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 creamy solid (1.4 g, 71%). 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=9.0 Hz, 1H), 7.34-7.5(m, 5H), 7.12-7.21(m, 4H), 7.05(dd, J=2.6, 9.0 Hz, 1H), 6.49(d, J=2.6 Hz, 1H), 4.17(m, 1H), 4.08(m, 1H), 3.19-3.27(m 2H), 2.73-2.83(m, 2H), 2.7(s, 3H), 1.22(s, 9H).

후처리

  1. additionwas added
  2. customthe mixture was quenched by addition of 1N NaOH aq (5 ml)
  3. additionThis was diluted to 60 ml with Et2O
  4. washwashed with H2O and brine
  5. dry with materialThe organic phase was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. customfiltrate evaporated to dryness under reduced pressure
  8. customThe residue was purified by flash column chromatography (SiO2, CH2Cl2)

출처 및 근거

ORD 기록
ord-fd8c9badfec34385960a19a55631f818
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09023848B2

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