Pyrrolidine → HCID 58418100, compound

HRID 1908750Notes

Reaction equation

HRID 1908750 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[N:10]=1)[C:5]([OH:7])=[O:6].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>[OH-].[Na+]>[CH3:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[N:10]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 1412092-Chloro-6-methylpyridine-4-carboxylic acid

Product 1

HCID 58418100HCID 58418100, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-chloro-6-methyl-isonicotinic acid (1.03 g, 5.98 mmol) in pyrrolidine (5 mL) is stirred at 85° C. for 6 days. The mixture is diluted with 1 N aq. NaOH (40 mL) and the solvent is removed in vacuo. The crude product is again dissolved in 1 N aq. NaOH (3 mL) and methanol (1 mL) and purified by MPLC on RP-C18-silica gel to give 2-methyl-6-pyrrolidin-1-yl-isonicotinic acid (1.18 g) as a beige solid; LC-MS: tR=0.52 min; [M+H]+=207.06; 1H NMR (D6-DMSO): δ 1.89-1.94 (m, 4H), 2.27 (s, 3H), 3.33-3.38 (m, 4H), 6.61 (s, 1H), 6.77 (s, 1H).

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe crude product is again dissolved in 1 N aq. NaOH (3 mL)
  3. custommethanol (1 mL) and purified by MPLC on RP-C18-silica gel

Sources & evidence

ORD record
ord-e6a93838b7784ef082c1f378fa3f1339
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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