Hydrochloric Acid → O-((4-Methoxyphenyl)methyl)hydroxylamine

HRID 457911

Reaction equation

HRID 457911 reaction equation
C([NH:8][OH:9])(OC(C)(C)C)=O.[H-].[Na+].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.Cl>C1COCC1.C(OCC)C>[NH2:8][O:9][CH2:18][C:17]1[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 120426O-((4-Methoxyphenyl)methyl)hydroxylamineYield 39%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution was made of Boc hydroxylamine (2.0 g, 17.1 mmol) in dry THF (60 ml). Sodium hydride (1.1 g of a 60% suspension in paraffin oil, 25.7 mmol) was then added and the suspension stirred. A catalytic amount of KI was then added to the reaction prior to the cautious addition of 4-methoxybenzyl chloride (3.2 g, 20.4 mmol). The reaction was then allowed to stir overnight before removal of solvent in vacuo. The residue was taken up with diethyl ether (100 ml) and HCl gas bubbled in for 20 minutes, causing the start of precipitation of the product. The flask was stoppered and left to stand overnight. The product was then filtered off as a off-white wax (39–52% yield according to varying batches).

Workup

  1. additionA catalytic amount of KI was then added to the reaction
  2. stirringto stir overnight before removal of solvent in vacuo
  3. custombubbled in for 20 minutes
  4. customthe start of precipitation of the product
  5. waitleft
  6. filtrationThe product was then filtered off as a off-white wax (39–52% yield according to varying batches)

Sources & evidence

ORD record
ord-478b9d3f88d142909d2dfdb80916c78b
Source dataset
uspto-grants-2007_03
Patent number
US07189754B2

Linked notes

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