Hydrochloric Acid → O-benzyl-N-(2,4,6-trimethoxy-benzyl)hydroxylamine

HRID 1816544

Reaction equation

HRID 1816544 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:4]=1[CH:5]=O.[CH2:15]([O:22][NH2:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>ClCCl>[CH2:15]([O:22][NH:23][CH2:5][C:4]1[C:3]([O:2][CH3:1])=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=1[O:13][CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 700192,4,6-TrimethoxybenzaldehydeHCID 102313O-BenzylhydroxylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 22494979O-benzyl-N-(2,4,6-trimethoxy-benzyl)hydroxylamineYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4,6-Trimethoxybenzaldehyde (12.42 g, 63.3 mmol) and O-benzylhydroxylamine (7.80 g, 63.3 mmol) were stirred in dichloromethane (65 mL) at rt overnight. The solvent was removed under reduced pressure. The crude residue was dissolved in ethanol (550 mL) and sodium cyanoborohydride (12.0 g, 189.9 mmol) was added dropwise. The mixture was stirred for 5-10 min, then 12 N HCl was added dropwise until pH became below 3. The reaction mixture was stirred for additional 3 h and 1 N NaOH was added until pH>8. The product was extracted with dichloromethane. The organic phase was dried over Na2SO4 and concentrated under vacuo. The residue was purified by flash chromatography (5% ether in dichloromethane) to give 15.9 g of O-benzyl-N-(2,4,6-trimethoxy-benzyl)hydroxylamine as an oil (83% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe crude residue was dissolved in ethanol (550 mL)
  3. stirringThe reaction mixture was stirred for additional 3 h
  4. extractionThe product was extracted with dichloromethane
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under vacuo
  7. customThe residue was purified by flash chromatography (5% ether in dichloromethane)

Sources & evidence

ORD record
ord-c82029e8226e4b60aef08c7dc6342d43
Source dataset
uspto-grants-2005_04
Patent number
US06884907B2

Linked notes

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