Hydroxylamine → N-Hydroxy-2-methyl-benzamidine

HRID 334542

Reaction equation

HRID 334542 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:10][OH:11].O.C(Cl)Cl.CO>CCO>[OH:11][N:10]=[C:4]([NH2:5])[C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 962WaterHCID 107212-MethylbenzonitrileHCID 21226129Dichloromethane methanol

Product 1

HCID 3098087N-Hydroxy-2-methyl-benzamidineYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-methyl-benzonitrile (0.950 mL, 8 mmol), hydroxylamine 50% in water (1.6 mL, 24 mmol) and EtOH (8 mL) was heated at 70° C. for 48 h. TLC analysis (DCM/MeOH: 97/3 as eluent) indicates the completion of the reaction. The solvent was removed under reduced pressure to afford 1.2 g of N′-hydroxy-2-methylbenzamidine (Yield: 100%) as a white powder (M.P.=147-148.5° C.). which can be used without further purification.

Workup

  1. customthe completion of the reaction
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-10ac7e740fc04206bbb1be61000b08d5
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Linked notes

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