Trifluoroacetic acid → 2-(6-Chloro-5-methylpyridin-3-yl)acetic acid

HRID 1036193Notes

Reaction equation

HRID 1036193 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]C(C)(C)C)=[O:10])=[CH:4][C:3]=1[CH3:16].C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[CH3:16]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 58447848Tert-butyl 2-(6-chloro-5-methylpyridin-3-yl)acetate

Product 1

HCID 552673572-(6-Chloro-5-methylpyridin-3-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-(6-chloro-5-methylpyridin-3-yl)acetate 86-6 (7.8 g, 32 mmol) and TFA (32 mL) in DCM (32 mL) was stirred at room temperature for 3 hours. The solution was adjusted to pH around 12 by sodium carbonate and extracted with dichloromethane. The aqueous phase was acidified to pH 3 by 1N HCl aqueous solution and stirred for 15 minutes. The suspension was extracted with dichloromethane (100 mL×3). The combined organic phases were washed with water and brine, dried over Na2SO4 and then dried to give 2-(6-chloro-5-methylpyridin-3-yl)acetic acid 86-7 as pale yellow solid. MS m/z 186.1 (M+1); 1H NMR 400 MHz (CD3Cl) δ 8.17 (d, 1H, J=2.0 Hz), 7.55 (d, 1H, J=2.0 Hz), 3.63 (s, 2H), 2.38 (s, 3H).

Workup

  1. extractionextracted with dichloromethane
  2. stirringstirred for 15 minutes
  3. extractionThe suspension was extracted with dichloromethane (100 mL×3)
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customdried

Sources & evidence

ORD record
ord-33605444110a4034906e1cab21fedbe0
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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