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

HRID 624192Notes

Reaction equation

HRID 624192 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-896d25df927643b19a9b7cb285d8a101
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

Loading…