Hydrochloric Acid → HCID 11298899, compound

HRID 1816538Notes

Reaction equation

HRID 1816538 reaction equation
[ClH:1].[C:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([N+:14]([O-])=O)[CH:5]=1)#[N:3].[H][H]>CO.O=[Pt]=O>[Cl-:1].[NH2:14][C:6]1[CH:5]=[C:4]([CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])[CH2:2][NH3+:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11356202Methyl 4-cyano-2-nitrobenzoateHCID 178418361HCID 178418361, compound3×

Product 1

HCID 11298899HCID 11298899, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

After addition of 365 ml of concentrated hydrochloric acid (4.37 mol) and 9 g of PtO2, a suspension of 900 g (4.37 mol) of methyl 4-cyano-2-nitrobenzoate in 13.5 l of methanol is first hydrogenated at room temperature at a hydrogen pressure of 1 bar. After the hydrogen uptake has subsided, the pressure is increased to 17 bar, and hydorgenation is continued until the hydrogen uptake is complete. For work-up, the pressure is released to atmospheric pressure, the catalyst is removed by filtration through silica gel and the filtrate is concentrated completely in vacuo. Digestion of the residue with ethyl acetate yields 3-amino-4-methoxycarbonylbenzylammonium chloride, yield 757 g (80%), melting point 185-190° C. (decomp.).

Workup

  1. temperaturethe pressure is increased to 17 bar, and hydorgenation
  2. customthe catalyst is removed by filtration through silica gel
  3. concentrationthe filtrate is concentrated completely in vacuo

Sources & evidence

ORD record
ord-15a481028c0643f5ae8987f5f9e64c65
Source dataset
uspto-grants-2005_04
Patent number
US06884903B2

Reaction notes

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