Hydrochloric Acid → HCID 67285287, compound

HRID 75055Notes

Reaction equation

HRID 75055 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([N+:9]([O-])=O)[CH:8]=1)[NH2:5].[ClH:12].[H][H]>[Rh].O>[ClH:12].[ClH:12].[CH3:1][CH:2]1[CH2:3][CH:4]([NH2:5])[CH2:6][CH:7]([NH2:9])[CH2:8]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 35650373-Methyl-5-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 67285287HCID 67285287, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The 3-methyl-5-nitroaniline (10.0 g, 65.7 mmol) was added to water (146 ml) and treated with 6N HCl (22.5 ml, 135.0 mmol) and 5% Rhodium on Alumina (1.9 g, 0.9 mmol). The mixture was charged to 105 atm of Hydrogen and heated to 100° C. for 19 hours. The reaction was cooled and filtered through celite and concentrated to dryness to give 5-methylcyclohexane-1,3-diamine dihydrochloride (12.9 g, 64.5 mmol) as a racemic mixture. The salt (6.5 g, 32.5 mmol) was dissolved in isopropyl alcohol (100 ml) and acetonitrile (100 ml) and treated with potassium carbonate (25.2 g, 182.0 mmol). The mixture was stirred at room temperature overnight, filtered thru celite, and concentrated in vacuo to afford 2.2 g of 5-methylcyclohexane-1,3-diamine as a racemic brown oil: LCMS RT=0.41 (M+1) 128.9.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through celite and
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8902a576ed3e467480506ae39bed7ac8
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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