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

HRID 592151Notes

Reaction equation

HRID 592151 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 X3). 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 X3)
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customdried

Sources & evidence

ORD record
ord-359cc81be84a431aa54a62b68251681f
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

Loading…