Hydrochloric Acid → methyl 2,3-dihydro-1H-isoindole-5-carboxylate hydrochloride

HRID 508571

반응식

HRID 508571 반응식
COC1C=CC(C[N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=3)[CH2:9]2)=CC=1.[ClH:23]>CO.[OH-].[OH-].[Pd+2]>[ClH:23].[CH2:9]1[C:10]2[C:15](=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=2)[CH2:16][NH:8]1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 58147238Methyl 2-(4-methoxybenzyl)isoindoline-5-carboxylate

생성물 1

HCID 19828495methyl 2,3-dihydro-1H-isoindole-5-carboxylate hydrochloride수율 2,242.3%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매2회HCID 887Methanol용매

실험 절차

To a mixture of methyl 2-(4-methoxybenzyl)isoindoline-5-carboxylate (0.82 g, 2.76 mmol) and 20% palladium hydroxide on carbon (0.194 g, 0.276 mmol) in methanol (25 mL) was added concentrated HCl (0.41 mL, 0.11 mmol). The mixture was degassed and stirred under a balloon atmosphere of H2 for two days. Additional 20% palladium hydroxide on carbon (0.08 g, 0.11 mmol) was then added and the reaction was continued for an additional day. The insolubles were removed via filtration through Clite and the solution was concentrated. Further drying under vacuum afforded a white powder (0.527 g, 91%). LCMS: (FA) ES+ 179. 1H NMR (d6-DMSO, 400 MHz) δ 9.71 (br s, 2H), 8.01 (s, 1H), 7.96 (d, J=8.0 Hz, 1H), 7.55 (d, J=7.7 Hz 2H), 4.56 (d, J=6.0 Hz, 4H), 3.87 (s, 3H).

후처리

  1. customThe mixture was degassed
  2. waitthe reaction was continued for an additional day
  3. customThe insolubles were removed via filtration through Clite
  4. concentrationthe solution was concentrated
  5. customFurther drying under vacuum

출처 및 근거

ORD 기록
ord-29d8c84632db486f9946cff7b9c082d5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096518B2

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