Sodium Hydroxide → 5-Chloro-2-(3-phenoxyazetidin-1-yl)nicotinic acid

HRID 72459

Reaction equation

HRID 72459 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67958085Methyl 5-chloro-2-(3-phenoxyazetidin-1-yl)nicotinate

Product 1

HCID 679582405-Chloro-2-(3-phenoxyazetidin-1-yl)nicotinic acidYield 95.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

Methyl 5-chloro-2-(3-phenoxyazetidin-1-yl)nicotinate (D75) (305 mg, 0.96 mmol) was dissolved in methanol/tetrahydrofuran (10 ml/10 ml), 5N NaOH (10 ml) was added at 0° C. The resulting reaction mixture was heated to 35° C. for 18 hours then cooled to room temperature and concentrated. Water added (10 ml) and the mixture was acidified with 2.5N HCl (pH1-2). The white solid was collected, washed with water and dried to provide compound (D101) (280 mg) as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. temperaturethen cooled to room temperature
  3. concentrationconcentrated
  4. additionWater added (10 ml)
  5. customThe white solid was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-fe99e9abad004c64a116bd86fea4ef4b
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Linked notes

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