Hydrochloric Acid → HCID 11298899, compound

HRID 1862590Notes

Reaction equation

HRID 1862590 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-bebd697a95864bc4a56fdab6a2c0a3a1
Source dataset
uspto-grants-2003_03
Patent number
US06538150B2

Reaction notes

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