Hydrochloric Acid → Methyl 4-methoxybenzimidate hydrochloride

HRID 472155

Reaction equation

HRID 472155 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[ClH:11].[CH3:12][OH:13]>>[ClH:11].[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7](=[NH:8])[O:13][CH3:12])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 701294-Methoxybenzonitrile

Product 1

HCID 12463133Methyl 4-methoxybenzimidate hydrochloride

Procedure

4-methoxybenzonitrile (12.5 g, 91.1 mmol) was dissolved in methanol (140 mL), through this cooled (−5° C.) solution gaseous HCl was bubbled for about 3 hours. The reaction mixture was then stirred, in a closed flask, at r.t. for 24 hours. Then the excess HCl was stripped by bubbling nitrogen and the resulting solution was concentrated, the residue was taken up with TBME (100 mL) and stirred for 30 min., then filtrated and dried to provide the title product as a colourless powder 19.0 g (quantitative). C9H11NO2.HCl, MW: 201.69 1H-NMR (300 MHz, D2O) ppm: 4.20 (s, 3H), 6.9 (m, 1H); 7.65 (m, 1H); 8.40 (m, 1H).

Workup

  1. customwas bubbled for about 3 hours
  2. customby bubbling nitrogen
  3. concentrationthe resulting solution was concentrated
  4. stirringstirred for 30 min.
  5. filtrationfiltrated
  6. customdried

Sources & evidence

ORD record
ord-34fa7fc0cc4b4f1d8abfbf868d16b1a0
Source dataset
uspto-grants-2014_01
Patent number
US08633208B2

Linked notes

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