Isatoic Anhydride → HCID 12431325, compound

HRID 650465Notes

Reaction equation

HRID 650465 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.Cl.[CH2:14]([O:21][NH2:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:22][O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:4]

Participants

5

Reactant 3

HCID 8359Isatoic Anhydride2×HCID 11430Potassium CarbonateHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 12431325HCID 12431325, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Reaction with isatoic anhydride: A mixture of isatoic anhydride (3.3 g, 20 mmol), O-benzylhydroxylamine hydrochloride (4.4 g, 27 mmol) and K2CO3 (6.9 g, 50 mmol) in 20 mL of DMF was stirred at rt until all the anhydride was consumed (ca. 2 days) by thin layer chromatographic analysis. The mixture was diluted with MTBE and washed with water and brine. After removal of solvent, the crude product was recrystallized from EtOAc/heptane to give 2-amino-N-benzyloxylbenzamide as a white solid (3.25 g, 67% yield).

Workup

  1. customwas consumed (ca. 2 days) by thin layer chromatographic analysis
  2. additionThe mixture was diluted with MTBE
  3. washwashed with water and brine
  4. customAfter removal of solvent
  5. customthe crude product was recrystallized from EtOAc/heptane

Sources & evidence

ORD record
ord-2117c44b96d4421abcc0cb2a02f4b99a
Source dataset
uspto-grants-2001_08
Patent number
US06274383B1

Reaction notes

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