4-Methoxybenzonitrile → HCID 178491258, compound

HRID 1172734Notes

Reaction equation

HRID 1172734 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.Cl.[NH2:21][OH:22]>CCO>[OH:22][NH:21][C:7](=[NH:8])[C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 701294-MethoxybenzonitrileHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178491258HCID 178491258, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 4-Methoxy-benzonitrile (1.07 g, 8 mmol) and DIEA (4.11 ml, 24 mmol) in EtOH (12.5 ml) was added 1.7 g of Hydroxylamine hydrochloride (24 mmol) and the reaction was heated at 70° C. for 48 h. Half of the solvent was removed under reduced pressure. The mixture was poured in DCM (100 ml) and water (30 ml). 2.5 ml of NaOH 1N was added until pH=9-10. The organic layer was separated and the aqueous phase was extracted with DCM. The organics layers were combined, washed with water, dried over MgSO4, filtered and evaporated under reduced pressure to afford 1.3 g (98%) of N-Hydroxy-4-methoxy-benzamidine as a colorless oil which can be used without further purification.

Workup

  1. customHalf of the solvent was removed under reduced pressure
  2. additionThe mixture was poured in DCM (100 ml)
  3. addition2.5 ml of NaOH 1N was added until pH=9-10
  4. customThe organic layer was separated
  5. extractionthe aqueous phase was extracted with DCM
  6. washwashed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f4b395cca72a4b94929cab7aab22b651
Source dataset
uspto-grants-2010_11
Patent number
US07834035B2

Reaction notes

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