Hydrochloric Acid → HCID 11298899, compound

HRID 1862593Notes

Reaction equation

HRID 1862593 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([N+:13]([O-])=O)[CH:4]=1)#[N:2].[H][H].[ClH:18]>O.[OH-].[Pd+2].[OH-]>[Cl-:18].[NH2:13][C:5]1[CH:4]=[C:3]([CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])[CH2:1][NH3+:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11356202Methyl 4-cyano-2-nitrobenzoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11298899HCID 11298899, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

Procedure

18.5 g (0.09 mol) of methyl 4-cyano-2-nitrobenzoate and 0.93 g of palladium hydroxide (20% on charcoal) are suspended in a mixture of 8 ml of concentrated hydrochloric acid (30% strength) and 315 ml of water in a Hastelloy stirred autoclave. Then, the mixture is hydrogenated at a hydrogen pressure of 17 bar until the hydrogen uptake is complete. After the pressure in the autoclave has been released and the catalyst filtered off, the filtrate is evaporated completely. This gives 19.5 g (97% strength) of 3-amino-4-methoxycarbonylbenzylammonium chloride of melting point 200-205° C.

Workup

  1. filtrationthe catalyst filtered off
  2. customthe filtrate is evaporated completely

Sources & evidence

ORD record
ord-147b25a5288c402282bd0617fad95400
Source dataset
uspto-grants-2003_03
Patent number
US06538150B2

Reaction notes

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