Citric Acid → HCID 86600598, compound

HRID 2377851Notes

Reaction equation

HRID 2377851 reaction equation
C(O[N:6]([C:18]1[C:19]([C:25]([O:27]C)=[O:26])=[CH:20][C:21]([Cl:24])=[N:22][CH:23]=1)[C:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13](OC)=[CH:12]C=1)=O)(C)(C)C.[OH-].[Na+].C(O)(=O)C[C:33](CC(O)=O)(C(O)=O)[OH:34]>CO>[Cl:24][C:21]1[CH:20]=[C:19]([C:25]([OH:27])=[O:26])[C:18]([NH:6][CH2:7][C:9]2[CH:10]=[CH:15][C:14]([O:34][CH3:33])=[CH:13][CH:12]=2)=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 86600599HCID 86600599, compound

Product 1

HCID 86600598HCID 86600598, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-{(tert-butoxy)-N-[(4-methoxyphenyl)-methyl]carbonylamino}-2-chloropyridine-4-carboxilate (1 equivalent) in MeOH, was added an aqueous solution of NaOH (3 equivalents). A precipitate formed immediately. The reaction was heated until the solution was clear and was then stirred for 1 hour at room temperature. Aqueous citric acid (1 M) was then added causing the product to crash out of solution. The product was then collected to afford the title compound in 77% yield.

Workup

  1. customA precipitate formed immediately
  2. temperatureThe reaction was heated until the solution
  3. customThe product was then collected

Sources & evidence

ORD record
ord-cd292013067f4c7abe8a56aad7edd118
Source dataset
uspto-grants-2008_12
Patent number
US07470709B2

Reaction notes

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