6-Aminohexanoic Acid → HCID 15992782, compound

HRID 986874Notes

Reaction equation

HRID 986874 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[OH-].[Na+].C(=O)(O)[O-].[Na+].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>O.C(O)C>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

7

Reactant 4

HCID 5646-Aminohexanoic AcidHCID 9590p-FluoronitrobenzeneHCID 14798Sodium HydroxideHCID 516892Sodium Bicarbonate

Product 1

HCID 15992782HCID 15992782, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5 g (38.11 mmol) of 6-aminocaproic acid are dissolved in 50 ml of water in the presence of 1.5 g (1 eq) of sodium hydroxide and 4.2 g (1.3 eq) of sodium bicarbonate in a 250 ml three-necked flask equipped with a reflux condenser and a thermometer. A solution of 4.9 ml (1.2 eq) of 4-fluoronitrobenzene in 50 ml of ethanol is run into the mixture, which mixture is subsequently brought to reflux (85°-90° C.) for 48 hours. The mixture is cooled and then extracted 3 times with dichloromethane. The aqueous phase is acidified to pH˜3 with 5N hydrochloric acid. A yellow precipitate is formed; the mixture is left overnight in a refrigerator. The precipitate is pulled dry and washed with water and with acetone. After drying, 9.3 g of a yellow product are obtained, i.e. a final yield of 97%.

Workup

  1. customequipped with a reflux condenser
  2. temperatureto reflux (85°-90° C.) for 48 hours
  3. temperatureThe mixture is cooled
  4. extractionextracted 3 times with dichloromethane
  5. customA yellow precipitate is formed
  6. customThe precipitate is pulled dry
  7. washwashed with water and with acetone
  8. customAfter drying

Sources & evidence

ORD record
ord-731370078f1649c8b61fa6fa034e07cf
Source dataset
uspto-grants-2003_10
Patent number
US06630004B1

Reaction notes

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