Hydrochloric Acid → 3-Bromo-6-methylpyridine-2-carboxylic acid

HRID 2175950Notes

Reaction equation

HRID 2175950 reaction equation
[Br:1][C:2]1C(C#N)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[OH-:11].[Na+].Cl.[CH3:14][CH2:15][OH:16]>>[Br:1][C:2]1[C:14]([C:15]([OH:11])=[O:16])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 219527473-Bromo-6-methylpyridine-2-carbonitrile

Product 1

HCID 219014933-Bromo-6-methylpyridine-2-carboxylic acid

Conditions

Temperature
90 °C

Procedure

To 3-bromo-6-methylpicolinonitrile (4 g, 20.3 mmol) in EtOH (40 mL) in a sealed tube was added aqueous 4M NaOH (15 mL). The reaction was heated at 90° C. for 24 h. Additional aqueous 4M NaOH was added and heating continued at 90° C. for 24 h. The reaction was cooled to rt, acidified to pH=3 with 1N HCl (aq), concentrated and used without further purification in subsequent steps. MS (ESI) mass calcd. for C7H6BrNO2, 216.0; m/z found 218 [M+H]+.

Workup

  1. temperatureheating
  2. temperatureThe reaction was cooled to rt
  3. concentrationconcentrated
  4. customused without further purification in subsequent steps

Sources & evidence

ORD record
ord-b9182a51068949f7b4b74d1045c6926f
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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