Ammonia → N1-[(5-methyl-2-furanyl)methyl]-1,2-benzenediamine

HRID 637397Notes

Reaction equation

HRID 637397 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)=[CH:4][CH:3]=1.S1C=CC=C1.N.[H][H]>CO.[Pd]>[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8030ThiopheneHCID 141828815-methyl-N-(2-nitrophenyl)-2-furanmethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 14182882N1-[(5-methyl-2-furanyl)methyl]-1,2-benzenediamineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 62 parts of 5-methyl-N-(2-nitrophenyl)-2-furanmethanamine, 2 parts of a solution of thiophene in methanol 4% and 400 parts of methanol, saturated with ammonia, was hydrogenated at normal pressure and at room temperature with 4 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 50.5 parts (95%) of N1 -[(5-methyl-2-furanyl)methyl]-1,2-benzenediamine as a residue (intermediate 8).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-6b684ff9ac6f4bfa9b70200cbd8aaa71
Source dataset
uspto-grants-1985_12
Patent number
US04556660

Reaction notes

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