Hydrochloric Acid → HCID 69044376, compound

HRID 69980Notes

Reaction equation

HRID 69980 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([O:16]C)=[O:15])=[N:4][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[Li+].[OH-].Cl>C1COCC1>[NH2:1][C:2]1[C:3]([C:14]([OH:16])=[O:15])=[N:4][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69046893Methyl 3-amino-6-cyclohexylpicolinate

Product 1

HCID 69044376HCID 69044376, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-amino-6-cyclohexylpicolinate (1.0 equiv) in THF, at a concentration of 0.5 M, was added 1M LiOH (4.0 equiv). After stirring for 4 hours at room temperature, 1 N HCl (4.0 equiv.) was added and the THF was removed in vacuo. The resulting solid was filtered, rinsed with cold H2O (3×20 mL) yielding 3-amino-6-cyclohexylpicolinic acid (18%). LCMS (m/z): 221.0 (MH+); LC Rt=4.1 min

Workup

  1. customthe THF was removed in vacuo
  2. filtrationThe resulting solid was filtered
  3. washrinsed with cold H2O (3×20 mL)

Sources & evidence

ORD record
ord-f8dfa6776d1c454da4bde06cd9d7087a
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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