Hydrochloric Acid → HCID 70005344, compound

HRID 986875Notes

Reaction equation

HRID 986875 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:6][CH:5]=1)([O-])=O.O.C1CCCCC=1.[ClH:26]>C(O)C.[Pd]>[ClH:26].[ClH:26].[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8079CyclohexeneHCID 15992782HCID 15992782, compound

Product 1

HCID 70005344HCID 70005344, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2 g (7.9 mmol) of 6-[N-(4-nitrophenyl)amino]caproic acid are partially dissolved in 40 ml of ethanol and 2 ml of water in a 150 ml three-necked flask equipped with a thermometer and a reflux condenser. 2 g of palladium-on-charcoal (10% active and 50% moisture) are then introduced, followed by 20 ml of cyclohexene. The mixture is brought to reflux for 2 hours and is then cooled, before being filtered through celite. After having run 4 ml (2.5 eq) of 5N hydrochloric acid onto the filtrate, the latter is evaporated to dryness and the residue is taken up in ethanol and precipitated from acetone. After filtration, 1.9 g of a white product are obtained, i.e. a final yield of 81%.

Workup

  1. temperatureto reflux for 2 hours
  2. temperatureis then cooled
  3. filtrationbefore being filtered through celite
  4. customthe latter is evaporated to dryness
  5. customprecipitated from acetone
  6. filtrationAfter filtration, 1.9 g of a white product
  7. customare obtained

Sources & evidence

ORD record
ord-4fcd329e8d3749adaa0217e226fb7fae
Source dataset
uspto-grants-2003_10
Patent number
US06630004B1

Reaction notes

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