Hydrochloric Acid → Methyl 5-(imino(methoxy)methyl)-2,4-dimethylbenzoate hydrochloride

HRID 541479Notes

Reaction equation

HRID 541479 reaction equation
[C:1]([C:3]1[C:4]([CH3:14])=[CH:5][C:6]([CH3:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].[ClH:15].[CH3:16][OH:17]>>[ClH:15].[NH:2]=[C:1]([O:17][CH3:16])[C:3]1[C:4]([CH3:14])=[CH:5][C:6]([CH3:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 68288737Methyl 5-cyano-2,4-dimethylbenzoate2×

Product 1

HCID 68288394Methyl 5-(imino(methoxy)methyl)-2,4-dimethylbenzoate hydrochlorideYield 15%

Procedure

Into a 50-mL three neck round-bottom flask, was placed a solution of methyl 5-cyano-2,4-dimethylbenzoate (compound 2.3, 900 mg, 4.28 mmol, 1.00 equiv, 90%) in methanol (20 mL). Hydrogen chloride gas was introduced by bubbling through the solution for 0.5 hr. The reaction mixture was then transferred into a 30-mL sealed tube and stirred overnight at room temperature. The mixture was concentrated under vacuum and the residue was diluted with ethyl acetate (30 mL) and extracted with water (10 mL). The aqueous was concentrated in vacuo to obtain the title compound as a white solid (200 mg, 15%).

Workup

  1. customby bubbling through the solution for 0.5 hr
  2. customsealed tube
  3. concentrationThe mixture was concentrated under vacuum
  4. additionthe residue was diluted with ethyl acetate (30 mL)
  5. extractionextracted with water (10 mL)
  6. concentrationThe aqueous was concentrated in vacuo

Sources & evidence

ORD record
ord-e7399ba79198477495344f4962884360
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

Loading…