2-Chloronicotinic acid → HCID 66703922, compound

HRID 425982Notes

Reaction equation

HRID 425982 reaction equation
[CH2:1]1[CH:5]2[CH2:6][CH:7]([NH2:8])[CH:3]([CH2:4]2)[CH2:2]1.Cl[C:10]1[N:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>[OH-].[Na+]>[C@H:3]12[CH2:4][C@H:5]([CH2:1][CH2:2]1)[CH2:6][C@H:7]2[NH:8][C:10]1[N:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 762582-Chloronicotinic acidHCID 98480Exo-2-bornanamine

Product 1

HCID 66703922HCID 66703922, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of exo-2-aminonorbornane and 2-chloronicotinic acid was stirred at 160° C. for 1 day and then spontaneously cooled. The reaction liquid was diluted with 1 M sodium hydroxide aqueous solution and then washed with diethyl ether. The water layer was neutralized with 1 M hydrochloric acid and then the precipitated crystals were collected by filtration to obtain rel-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamino]nicotinic acid.

Workup

  1. temperaturespontaneously cooled
  2. customThe reaction liquid
  3. washwashed with diethyl ether
  4. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-65a3c2d01ca24c6ab7dcd1672e3d5a75
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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