Benzyloxyamine hydrochloride → N-[4-[(E)-phenylmethoxyiminomethyl]phenyl]-1,3-dihydroisoindole-2-carboxamide

HRID 624192노트

반응식

HRID 624192 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)=[O:11])=[CH:5][CH:4]=1)=O.Cl.[CH2:22]([O:29][NH2:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])(=O)C.[Na+]>CO.O>[CH2:22]([O:29]/[N:30]=[CH:1]/[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)=[O:11])=[CH:5][CH:4]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

6

반응물 3

HCID 102312Benzyloxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86665079N-(4-formylphenyl)isoindoline-2-carboxamide

생성물 1

HCID 57510176N-[4-[(E)-phenylmethoxyiminomethyl]phenyl]-1,3-dihydroisoindole-2-carboxamide

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

실험 절차

In a 8 mL sealed vial was mixed N-(4-formylphenyl)isoindoline-2-carboxamide (50 mg, 0.188 mmol) in methanol (1 ml). A solution of O-benzylhydroxylamine hydrochloride (45.0 mg, 0.282 mmol) and sodium acetate (46.0 mg, 0.338 mmol) in water (1.000 ml) was then added and the reaction was stirred overnight at room temperature. The reaction was diluted with water and the product was extracted with dichloromethane. The organic layer was washed with brine, dried with sodium sulfate, decanted, and concentrated. Purification by chromatography provided the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.55 (s, 1H), 8.21 (s, 1H), 7.65 (m, 2H), 7.50 (m, 2H), 7.44-7.28 (m, 9H), 5.14 (s, 2H), 4.78 (bs, 4H); MS (ESI(+)) m/e 372 (M+H)+.

후처리

  1. customIn a 8 mL sealed vial
  2. extractionthe product was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried with sodium sulfate
  5. customdecanted
  6. concentrationconcentrated
  7. customPurification by chromatography

출처 및 근거

ORD 기록
ord-896d25df927643b19a9b7cb285d8a101
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302989B2

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