Hydrochloric Acid → (5-Bromo-6-methoxy-pyridin-3-yl)-acetic acid

HRID 2204339Notes

Reaction equation

HRID 2204339 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]#N)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].[OH-:13].[K+].Cl.[OH2:16]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:16])=[O:13])[CH:5]=[N:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 585393925-Bromo-6-methoxy-3-pyridineacetonitrile

Product 1

HCID 82664957(5-Bromo-6-methoxy-pyridin-3-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of (5-bromo-6-methoxy-pyridin-3-yl)-acetonitrile (Step AM1) (6.61 mmol) in EtOH (19 mL) was added a solution of KOH (26.7 mmol) in H2O (19 mL) and the mixture was stirred at 80° C. for 45 min. After cooling to rt, the pH was adjusted to 3-4 with 1M aqueous HCl and the mixture was extracted with CH2Cl2 (2×). The combined organic layers were dried (MgSO4), filtered and concentrated to afford the title compound. ESI-MS: tR=0.75 min, [M+H]+ 246/248 (LC-MS 1).

Workup

  1. temperatureAfter cooling to rt
  2. extractionthe mixture was extracted with CH2Cl2 (2×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-853c5cd6c14c4984be132999887ea759
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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