Hydrochloric Acid → HCID 90414726, compound

HRID 1746076Notes

Reaction equation

HRID 1746076 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[C:17]3[O:16][CH2:15][O:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:18]([O:20]C)=[O:19])[C:3]=1[Cl:22].[OH-].[Na+].Cl>CO>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[C:17]3[O:16][CH2:15][O:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:18]([OH:20])=[O:19])[C:3]=1[Cl:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90413471HCID 90413471, compound

Product 1

HCID 90414726HCID 90414726, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a reaction vessel containing methyl 4-amino-6-(benzo[d][1,3]dioxol-4-yl)-3-chloro-5-fluoropicolinate (0.150 g, 0.462 mmol) was added methanol (9.24 mL) and 2 N sodium hydroxide (0.924 mL, 1.848 mmol). The reaction mixture was stirred overnight at room temperature, neutralized to pH 3 with 2 N HCl, and concentrated under a stream of nitrogen. The precipitate that formed was filtered off, washed with water, and dried to provide the title compound as a white solid (0.107 g, 74.6%): mp 171-173° C.; 1H NMR (400 MHz, DMSO-d6) δ 7.08-7.00 (m, 2H), 6.99-6.93 (m, 2H), 6.93 (br s, 2H), 6.06 (s, 2H); ESIMS m/z 311.2 ([M+H]+), 309.1 ([M−H]−).

Workup

  1. concentrationconcentrated under a stream of nitrogen
  2. customThe precipitate that formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b86c115d6afd41cf98340c98b8775f96
Source dataset
uspto-grants-2015_10
Patent number
US09149038B2

Reaction notes

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