Hydrochloric Acid → HCID 178515143, 화합물

HRID 853706

반응식

HRID 853706 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[CH2:13][CH2:12][C:11]2=[O:16])=[CH:4][CH:3]=1.C[O:18][C:19]([C:21]1[C:26]([C:27](OC)=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=1)=O.[H-].[Na+].Cl>O1CCCC1.C(OCC)C.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[C:13]3[C:19]([OH:18])=[C:21]4[C:26]([CH:25]=[CH:24][CH:23]=[N:22]4)=[C:27]([OH:28])[C:12]=3[C:11]2=[O:16])=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 690582,3-Dimethyl 2,3-pyridinedicarboxylateHCID 589289521-[2-(4-Fluoro-phenyl)-ethyl]-pyrrolidine-2,5-dione

생성물 1

HCID 178515143HCID 178515143, 화합물수율 58%

시약·촉매·용매 3

HCID 887Methanol용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

To 1-[2-(4-Fluoro-phenyl)-ethyl]-pyrrolidine-2,5-dione 309 (270 mg, 1.22 mmol and pyridine-2,3-dicarboxylic acid dimethyl ester (261.6 mg, 1.34 mmol) dissolved in tetrahydrofuran (12.0 ml) and methanol (1.4 ml) was added a 60% dispersion of sodium hydride in mineral oil (108 mg, 2.7 mmol). The reaction mixture was warmed to 80° C. and kept at 80° C. with stirring overnight. The reaction mixture was then placed in an ice bath and titrated to a pH of 4 with 1 M HCl. Two hundred (200) ml of diethylether was then added and the resulting yellow solid was collected by filtration. The solid was washed twice with ether, twice with water, and dried under high vacuum with heating to provide 7-[2-(4-fluoro-phenyl)-ethyl]-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione 310 (250 mg, 0.71 mmol, 58%). 1H NMR (d-DMSO) δ 10.7 (broad, 1H), 8.98 (dd, 1H), 8.66 (dd, 1H), 7.73 (m, 1H), 7.18 (m, 2H), 7.04 (t, 2H), 3.72 (t, 2H), 2.86 (t, 2H). MS: 353.1 (M+1).

후처리

  1. customkept at 80° C.
  2. customThe reaction mixture was then placed in an ice bath
  3. filtrationthe resulting yellow solid was collected by filtration
  4. washThe solid was washed twice with ether, twice with water
  5. customdried under high vacuum
  6. temperaturewith heating

출처 및 근거

ORD 기록
ord-9803244f792e4dc5b3604b85b4a2777d
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253180B2

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