Hydrochloric Acid → HCID 178491259, compound

HRID 1821132Notes

Reaction equation

HRID 1821132 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].Cl.[NH2:14][OH:15].C([O-])([O-])=O.[K+].[K+].Cl>C(O)C>[OH:15][NH:14][C:5](=[NH:6])[C:4]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 777502,4-DimethoxybenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178491259HCID 178491259, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2,4-dimethoxybenzonitrile (3.25 g, 20 mmol), hydroxylamine hydrochloride (2.92 g, 42 mmol) and K2CO3 (5.80 g, 42 mmol) in ethanol (80 mL) is stirred at 85° C. for 27 h before it is poured onto water (250 mL). The solution is acidified by adding 1 N aq. HCl (75 mL) and extracted once with DCM (100 mL). The aq. layer is basified with 1 N aq. NaOH (90 mL) and extracted three times with DCM (3×150 mL). The organic extracts are dried over MgSO4, the solvent is evaporated and the residue is dried under high vacuum to leave N-hydroxy-2,4-dimethoxy-benzamidine (1.35 g) as a beige solid. LC-MS: tR=0.68 min, [M+1]+=197.11.

Workup

  1. additionis poured onto water (250 mL)
  2. extractionextracted once with DCM (100 mL)
  3. extractionextracted three times with DCM (3×150 mL)
  4. dry with materialThe organic extracts are dried over MgSO4
  5. customthe solvent is evaporated
  6. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-dd4c043214fc4bb6b419fdb0be512cca
Source dataset
uspto-grants-2009_10
Patent number
US07605269B2

Reaction notes

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