Sodium Hydroxide → 3-Chloro-6-(pivalamidomethyl)picolinic acid

HRID 1469714Notes

Reaction equation

HRID 1469714 reaction equation
[Cl:1][C:2]1[C:3]([C:16]([O:18]CC)=[O:17])=[N:4][C:5]([CH2:8][NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:7]=1.[OH-].[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[C:3]([C:16]([OH:18])=[O:17])=[N:4][C:5]([CH2:8][NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86692225Ethyl 3-chloro-6-(pivalamidomethyl)picolinate

Product 1

HCID 866922263-Chloro-6-(pivalamidomethyl)picolinic acidYield 82.7%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The title compound was prepared following the procedure described in Step 3 of Intermediate-2 using ethyl 3-chloro-6-(pivalamidomethyl)picolinate (1.00 g, 3.35 mmol) in THF:MeOH:H2O (3:2:1; 6 mL) and NaOH (268 mg, 6.71 mmol) to afford 750 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 13.85 (br s, 1H), 8.25 (br t, 1H), 7.99 (d, J=8.4 Hz, 1H), 7.29 (d, J=8.1 Hz, 1H), 4.32 (d, J=6.0 Hz, 2H), 1.19 (s, 9H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-fa30a42fe7d64e17b5530bfa9b069480
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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