2-Amino-5-methylbenzoic acid → 2-Carboxy-4-methylcyclohexan-1-yl-amine

HRID 22423

Reaction equation

HRID 22423 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H][H]>O1CCCC1.[Ru].C>[C:4]([CH:3]1[CH2:7][CH:8]([CH3:11])[CH2:9][CH2:10][CH:2]1[NH2:1])([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 762552-Amino-5-methylbenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 149939762-Carboxy-4-methylcyclohexan-1-yl-amine

Reagents, catalysts & solvents 2

HCID 16218582Ruthenium carbonCatalystHCID 8028TetrahydrofuranSolvent

Procedure

50 g (0.33 mol) of 2-amino-5-methyl-benzoic acid, dissolved in 100 ml of tetrahydrofuran, are hydrogenated for 14 hours at 200° C. and 200 bar hydrogen in the presence of 5 g of ruthenium/charcoal. After cooling and evaporation, 30 g o f 2-carboxy-4-methyl-cyclohexan-1-yl -amine are obtained as a pale oil.

Workup

  1. temperatureAfter cooling
  2. customevaporation, 30 g o f 2-carboxy-4-methyl-cyclohexan-1-yl -amine
  3. customare obtained as a pale oil

Sources & evidence

ORD record
ord-7803faf4114942328d46e35a1e9d6188
Source dataset
uspto-grants-1995_06
Patent number
US05428073

Linked notes

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