6-Chloropicolinic acid → HCID 62234692, compound

HRID 530443Notes

Reaction equation

HRID 530443 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C.[NH2:26][CH2:27][CH:28]1[CH2:30][CH2:29]1>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH:26][CH2:27][CH:28]2[CH2:30][CH2:29]2)=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 208126-Chloropicolinic acidHCID 65578Oxalyl chlorideHCID 75646CyclopropanemethanamineHCID 81531Diisopropylethylamine

Product 1

HCID 62234692HCID 62234692, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

6-Chloropyridine-2-carboxylic acid (5.00 g, 31.7 mmol) was dissolved in DCM (100 mL) and DMF (0.5 mL) and oxalyl chloride (6.54 mL, 76.2 mmol) were added dropwise. The reaction mixture was stirred for 2 h, concentrated in vacuo and azeotroped with DCM. The residue was dissolved in DCM (100 mL), DIPEA (22.6 mL, 127 mmol) and aminomethylcyclopropane (5.51 mL, 63.5 mmol) were added dropwise and the reaction mixture was stirred for 4 h. The reaction mixture was washed with sat aq NaHCO3 solution (250 mL), dried (MgSO4) and concentrated in vacuo to give the crude title compound (6.50 g, 97%) as a light brown gum. LCMS (ES+): 211.2 [MH]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customazeotroped with DCM
  3. dissolutionThe residue was dissolved in DCM (100 mL)
  4. stirringthe reaction mixture was stirred for 4 h
  5. washThe reaction mixture was washed with sat aq NaHCO3 solution (250 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09bdf6feef204b6b941c6d4f5c034854
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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