Sodium Carbonate → N-Hydroxy-2-methoxy-N-methyl-benzamidine

HRID 1822699Notes

Reaction equation

HRID 1822699 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6].Cl.[CH3:12][NH:13]O.C(=O)([O-])[O-].[Na+].[Na+].[OH2:21].C(O)C>>[OH:21][N:13]([CH3:12])[C:5](=[NH:6])[C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 77906N-methylhydroxylamine hydrochlorideHCID 810862-MethoxybenzonitrileHCID 19096565Water ethanol

Product 1

HCID 22169629N-Hydroxy-2-methoxy-N-methyl-benzamidine

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-methoxybenzonitrile (2.66 g, 20 mmol) and N-methylhydroxylamine hydrochloride (3.341 g, 40 mmol) in 2:1 water/ethanol (30 mL) was added sodium carbonate (2.332 g, 22 mmol) in small portions and the resulting pink solution stirred at 80° C. for 28 h. The reaction mixture was then concentrated and the residue stirred with CH2Cl2, filtered and concentrated to give crude product as a purple solid (3.3 g), which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. stirringthe residue stirred with CH2Cl2
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-664fb51943874ab7afcd47701f7f7e30
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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