Sodium Hydroxide → HCID 50995122, compound

HRID 1807383Notes

Reaction equation

HRID 1807383 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1)[CH3:5].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[I:12][C:9]1[CH:8]=[CH:7][C:6]([CH:4]([NH:3][O:2][CH3:1])[CH3:5])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86761751HCID 86761751, compound

Product 1

HCID 50995122HCID 50995122, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 1-(4-iodo-phenyl)-ethanone O-methyl-oxime (2.17 g, 7.83 mmol) in glacial acetic acid (22 ml), Sodium cyano borohydride (1.54 g, 24.39 mmole) was added portion wise at 15° C. and stirred for 12 hours at ambient temperature. Acetic acid was removed by distillation. The resulting reaction mass was basified with 10% aq. NaOH solution at 10-15° C. Aqueous layer was extracted with EtOAc (3×30 ml). The combined organic layer was washed with brine (2×30 ml) and dried over sodium sulfate. The organic layer was concentrated under vacuum to give pale yellow liquid, which was purified by chromatography to afford 2.1 g (96% of theory) of N-[1-(4-Iodo-phenyl)-ethyl]-O-methyl-hydroxylamine.

Workup

  1. customAcetic acid was removed by distillation
  2. customThe resulting reaction mass
  3. extractionAqueous layer was extracted with EtOAc (3×30 ml)
  4. washThe combined organic layer was washed with brine (2×30 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic layer was concentrated under vacuum
  7. customto give pale yellow liquid, which
  8. customwas purified by chromatography

Sources & evidence

ORD record
ord-d1274ad506cc420086001812f7524a03
Source dataset
uspto-grants-2013_01
Patent number
US08357634B2

Reaction notes

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