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

HRID 624192ノート

反応式

HRID 624192 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-896d25df927643b19a9b7cb285d8a101
出典データセット
uspto-grants-2016_04
特許番号
US09302989B2

反応ノート

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