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Stannous chloride dihydrate → HCID 49846267, 화합물

HRID 1926694
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HRID 1926694 반응식
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([Br:12])=[CH:8][CH:9]=2)[N:4]([OH:13])[C:3]1=[O:14].Cl.NC(CC1C=CC(Br)=CC=1[N+]([O-])=O)C(O)=O.O.O.[Sn](Cl)Cl>CCO>[NH2:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([Br:12])=[CH:8][CH:9]=2)[N:4]([OH:13])[C:3]1=[O:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 61436Stannous chloride dihydrateHCID 1276138382420-39-1HCID 12761396HCID 12761396, 화합물

생성물 1

HCID 49846267HCID 49846267, 화합물수율 58%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

3-Amino-7-bromo-1-hydroxy-3,4-dihydroquinolin-2(1H)-one (26) To a solution of 2-amino-3-(4-bromo-2-nitrophenyl)propanoic acid, hydrochloride salt (25) (343 mg, 1.06 mmol) in EtOH (10 mL) was added tin(II) chloride dihydrate (541 mg, 2.40 mmol), and the reaction was stirred at RT overnight. It was then quenched with aqueous ammonium hydroxide (1.5 mL), and the resulting precipitate was removed via filtration and washed with MeOH. The combined filtrates were concentrated in vacuo, and the residue was purified by chromatography on silica gel to provide the title product as a white powder (161 mg, 58%). LCMS m/z 258.9 (M+1). 1H NMR (500 MHz, DMSO-d6) δ 2.71 (dd, J=15.4, 12.9 Hz, 1H) 2.99 (dd, J=15.6, 6.1 Hz, 1H), 3.56 (dd, J=12.8, 6.0 Hz, 1H) 7.17-7.21 (m, 2H), 7.28 (d, J=1.7 Hz, 1H).

후처리

  1. customIt was then quenched with aqueous ammonium hydroxide (1.5 mL)
  2. customthe resulting precipitate was removed via filtration
  3. washwashed with MeOH
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. customthe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-ba238dab1562458899952cdbcefe817a
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183238B2

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