N-methyl-2-pyrrolidone → HCID 67026994, compound

HRID 1908737Notes

Reaction equation

HRID 1908737 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6](Cl)[CH:5]=1.CN1C(=O)CCC1.[CH2:21]([Mg]Cl)[CH:22]([CH3:24])[CH3:23]>C1COCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH:5]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 13339618Methyl 2-chloro-6-methoxyisonicotinateHCID 178418368HCID 178418368, compound

Product 1

HCID 67026994HCID 67026994, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-chloro-6-methoxy-isonicotinic acid methyl ester (1.66 g, 8.23 mmol) in dry THF (50 mL), Fe(acac)3 (320 mg, 0.901 mmol) followed by NMP (1.1 mL, 11.5 mmol) is added. The mixture is cooled to −74° C. before a 2 M solution of isobutylmagnesium chloride (7 mL, 14.0 mmol) in THF is added. Stirring is continued at −75° C. for 1 h, before the mixture is warmed to 0° C. The reaction is quenched by carefully adding water. The mixture is diluted with EA, washed with water followed by brine, dried over MgSO4, filtered and concentrated to give crude 2-isobutyl-6-methoxy-isonicotinic acid methyl ester (1.20 g) as an oil; LC-MS: tR=1.37 min; [M+1]+=224.12.

Workup

  1. additionis added
  2. additionis added
  3. customThe reaction is quenched by carefully adding water
  4. additionThe mixture is diluted with EA
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fdcf6a2035b3433e84052a4822052180
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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