Lithium hydroxide, monohydrate → 2-(2-Benzylpyrrolidin-1-yl)-5-chloronicotinic acid

HRID 72458Notes

Reaction equation

HRID 72458 reaction equation
[CH2:1]([CH:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]1[N:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:14]=1[C:15]([O:17]C)=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCOCC1.O>[CH2:1]([CH:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]1[N:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:14]=1[C:15]([OH:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67958110HCID 67958110, compound

Product 1

HCID 679582562-(2-Benzylpyrrolidin-1-yl)-5-chloronicotinic acidYield 97.8%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
150 °C

Procedure

To methyl 2-(2-benzylpyrrolidin-1-yl)-5-chloronicotinate (D74) (75 mg, 0.226 mmol) in a mixture 1,4-dioxane/water (3 ml/1 ml), lithium hydroxide monohydrate (14.3 mg, 0.34 mmol) was added and the resulting mixture was stirred at 150° C. under microwave irradiation for 10 min (2 cycles of 5 min each). Solvents were evaporated in vacuo. The obtained residue was diluted with water/1M HCl (5 ml/15 ml) and extracted with ethyl acetate (3×30 ml). Collected fractions after solvent evaporation afforded the title compound (D100) (70 mg).

Workup

  1. customSolvents were evaporated in vacuo
  2. additionThe obtained residue was diluted with water/1M HCl (5 ml/15 ml)
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-faad08b707b74956ab0ae72080a6a1e1
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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