Hydroxylamine → 2-Benzyloxy-3,4-dimethoxybenzonitrile

HRID 2228506Notes

Reaction equation

HRID 2228506 reaction equation
C([O-])(=O)C.[Na+].[NH2:6]O.[CH2:8]([O:15][C:16]1[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=[CH:20][C:17]=1[CH:18]=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>C(O)(=O)C>[CH2:8]([O:15][C:16]1[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=[CH:20][C:17]=1[C:18]#[N:6])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 962WaterHCID 517045Sodium AcetateHCID 8195792-(Benzyloxy)-3,4-dimethoxybenzaldehyde

Product 1

HCID 184706112-Benzyloxy-3,4-dimethoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A slurry of sodium acetate (17.06 g, 0.208 mol) and hydroxylamine (14.45 g, 0.208 mol) in glacial acetic acid (120 ml) was added to 2-benzyloxy-3,4-dimethoxybenzaldehyde (28.3 g, 0.104 mol) and the resulting suspension stirred at reflux for 18 hours. On cooling, water (250 ml) was added and the mixture extracted with dichloromethane (500 ml). The combined organic extracts were dried (MgSO4), filtered and evaporated under reduced pressure. The crude product was purified on silica gel eluting with hexane:ethyl acetate (80:20 v/v) to give the subtitle compound as an oil that crystallised on standing (21.06 g, 75%). Rf 0.52 (ethyl acetate:hexane, 1:1, v/v). MS m/z 270 (MH)+.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureOn cooling
  3. extractionthe mixture extracted with dichloromethane (500 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude product was purified on silica gel eluting with hexane:ethyl acetate (80:20 v/v)

Sources & evidence

ORD record
ord-9320c1cd8f9b4fd6b96e6ee831b34260
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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