Hydrochloric Acid → HCID 90011309, compound

HRID 1054912Notes

Reaction equation

HRID 1054912 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[C:7]([N+:13]([O-])=O)=[N:8][C:9]([Br:12])=[CH:10][CH:11]=1.Cl.C(=O)(O)[O-].[Na+]>CO.[Fe]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[C:7]([NH2:13])=[N:8][C:9]([Br:12])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 90011186(6-Bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester

Product 1

HCID 90011309HCID 90011309, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

(6-Bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester (10.9 g, 37.5 mmol) was dissolved in methanol (90 mL). Concentrated HCl (10 mL) was then added followed by iron (6.4 g, 110 mmol). The reaction mixture was stirred at 60° C. for 1 hour. Then, the reaction mixture was cooled to room temperature and neutralized with solid sodium bicarbonate. The insoluble iron salts were removed by centrifugation. Silica gel was then added to the supernatant and the solvents were removed under reduced pressure. The resulting crude material was purified by column chromatography (SiO2, EtOAc/hexanes) to give (2-amino-6-bromopyridin-3-yloxy)acetic acid methyl ester. Yield 4.0 g (15 mmol, 40%). LCMS (ESI): calc. C8H9BrN2O3=260, 262; obs. M+H=261, 263.

Workup

  1. customThe insoluble iron salts were removed by centrifugation
  2. additionSilica gel was then added to the supernatant
  3. customthe solvents were removed under reduced pressure
  4. customThe resulting crude material was purified by column chromatography (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record
ord-5e0bf88fb9bb48c591a353ace90aeff0
Source dataset
uspto-grants-2016_07
Patent number
US09394315B2

Reaction notes

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