Hydrochloric Acid → HCID 71150428, compound

HRID 407240Notes

Reaction equation

HRID 407240 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:5]=[C:4]([C:19]([O:21]C)=[O:20])[C:3]=1[O:23][CH3:24].[OH-].[Na+].Cl>CO>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:5]=[C:4]([C:19]([OH:21])=[O:20])[C:3]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71150713HCID 71150713, compound

Product 1

HCID 71150428HCID 71150428, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-3-methoxypicolinate (0.77 g, 2.15 mmol) was dissolved in CH3OH (14 mL) and 2 N sodium hydroxide (NaOH; 4.3 mL) was added. The solution was stirred at room temperature overnight, acidified with 2 N HCl and concentrated to remove the majority of CH3OH. The precipitate that formed was filtered, washed with H2O and dried under vacuum to provide the title compound as a white solid (668 mg, 90%): mp 143-146° C.; 1H NMR (400 MHz, CDCl3) δ 7.30 (dd, J=8.5, 1.6 Hz, 1H), 7.19 (dd, J=8.4, 6.8 Hz, 1H), 4.83 (s, 2H), 4.07 (s, 3H), 4.02 (d, J=1.1 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ −128.66, −128.74, −134.93, −135.01; ESIMS m/z 345 ([M+H]+), 343 ([M−H]−).

Workup

  1. concentrationconcentrated
  2. customto remove the majority of CH3OH
  3. customThe precipitate that formed
  4. filtrationwas filtered
  5. washwashed with H2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6d501d0a14c84ab2873b34d9de7d03e3
Source dataset
uspto-grants-2014_06
Patent number
US08754229B2

Reaction notes

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