Hydrochloric Acid → 7-(2-Pyridylamino)heptanoic acid

HRID 1057482Notes

Reaction equation

HRID 1057482 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[OH-].[Na+].Cl>N1C=CC=CC=1>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97462-FluoropyridineHCID 135807-Aminoheptanoic acidHCID 14798Sodium Hydroxide

Product 1

HCID 186713897-(2-Pyridylamino)heptanoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring solution of 7-aminoheptanoic acid in pyridine (0.5 M) was added 2-fluoropyridine (2 eq) and 2N NaOH (1 eq), and the reaction was refluxed overnight. The mixture was adjusted to neutral pH with 6N HCl and concentrated in vacuo. The residue was suspended in 10:1:1 EtOH/NH4OH/H2O, filtered through a plug of silica, and concentrated in vacuo to afford a colorless solid.

Workup

  1. temperaturethe reaction was refluxed overnight
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered through a plug of silica
  4. concentrationconcentrated in vacuo
  5. customto afford a colorless solid

Sources & evidence

ORD record
ord-02f2540348bf455fac9a3858e825fa23
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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