1,2-Dichloroethane → HCID 86643312, compound

HRID 1803055Notes

Reaction equation

HRID 1803055 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]([OH:11])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH3:13][NH:14][O:15][CH3:16].CN1CCOCC1.C(Cl)CCl>C(Cl)Cl>[Cl:1][C:2]1[C:7]([CH2:8][C:9]([N:14]([O:15][CH3:16])[CH3:13])=[O:11])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 147395442-(2-Chloropyridin-3-yl)acetic acid2×

Product 1

HCID 86643312HCID 86643312, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of (2-chloropyridin-3-yl)acetic acid (Intermediate 3; 2.0 g, 11.6 mmol) in DCM (100 mL) was added N,O-dimethylhydroxylamine hydrochloride (1.19 g, 12.2 mmol), N-methylmorpholine (3.8 mL, 34.8 mmol) and EDC (2.3 g, 12.2 mmol). The mixture was stirred at room temperature for 48 hours, diluted with DCM (100 mL), washed with 10% HCl (aq) solution (200 mL) and brine (200 mL), dried (Na2SO4), filtered and the solvents removed in vacuo. The crude product was purified by column chromatography (SiO2, 1:1 EtOAc:DCM) to give the title compound as a white waxy solid (2.2 g, 88%). δH (DMSO-d6) 8.31 (1H, dd, J 4.7, 1.9 Hz), 7.81 (1H, dd, J 7.5, 1.9 Hz), 7.40 (1H, dd, J 7.5, 4.7 Hz), 3.93 (2H, s), 3.76 (3H, s), 3.15 (3H, s). LCMS (pH 3) RT 2.22 minutes, (ES+) 215 35Cl (M+H)+, 217 37Cl (M+H)+.

Workup

  1. washwashed with 10% HCl (aq) solution (200 mL) and brine (200 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvents removed in vacuo
  5. customThe crude product was purified by column chromatography (SiO2, 1:1 EtOAc:DCM)

Sources & evidence

ORD record
ord-cd39ed9b767f4796b63f4fa2553c8ce5
Source dataset
uspto-grants-2013_01
Patent number
US08350037B2

Reaction notes

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