Water → HCID 86669112, compound

HRID 530753Notes

Reaction equation

HRID 530753 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([Cl:9])[N:6]=[C:5]([C:10]([OH:12])=O)[CH:4]=1.C1N=C[N:15](C(N2C=NC=C2)=O)C=1.[NH4+].[OH-].O>CN(C=O)C.C(Cl)Cl>[Cl:9][C:7]1[N:6]=[C:5]([C:10]([NH2:15])=[O:12])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 230023686-Chloro-4-methoxypyridine-2-carboxylic acid

Product 1

HCID 86669112HCID 86669112, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-6-chloro picolinic acid (25 mmol) in anhydrous DMF (48 mL) was added CDI (27.5 mmol) at 0° C. The reaction mixture was stirred for 5 min in an ice-bath and then stirred at room temperature. After the reaction was completed, NH4OH (190 mL) was added and the reaction mixture was stirred at room temperature for 6 hrs. The mixture was partioned between H2O (200 mL) and DCM (300 mL). The organic layer was washed with H2O and brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude was purified by silica gel chromatography (eluent: DCM/CH3OH) to give compound 18 as a beige solid in 61% yield. MS (ESI, EI+): m/z=187.14 (MH+).

Workup

  1. stirringstirred at room temperature
  2. stirringthe reaction mixture was stirred at room temperature for 6 hrs
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by silica gel chromatography (eluent: DCM/CH3OH)

Sources & evidence

ORD record
ord-d72f82637a0c4fe48e73c07daef9fb35
Source dataset
uspto-grants-2016_05
Patent number
US09353100B2

Reaction notes

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