Hydrochloric Acid → HCID 66835474, compound

HRID 536278Notes

Reaction equation

HRID 536278 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[O-:12][CH2:13][CH3:14].[Na+].Cl>C(O)C>[Br:1][C:2]1[C:3]([O:12][CH2:13][CH3:14])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 2723922Sodium ethoxide2×

Product 1

HCID 66835474HCID 66835474, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A slurry of 5-bromo-6-chloronicotinic acid (240 mg, 1.0 mmol) and sodium ethoxide (138 mg, 2.0 mmol) in anhydrous ethanol (2 mL) was heated under microwave conditions at 100° C. for 15 min; an additional portion of sodium ethoxide (79 mg, 1.0 mmol) was added and heating was continued for 1 hr. After cooling the reaction mixture was adjusted to a pH of 4 with 1 N aqueous hydrochloric acid, the resulting solids collected and dried in vacuo to afford 5-bromo-6-ethoxynicotinic acid (140 mg). 1H NMR (400 MHz, DMSO-d6) d ppm 1.33 (t, J=7.02 Hz, 3H) 4.43 (q, J=7.09 Hz, 2H) 8.32 (d, J=2.15 Hz, 1H) 8.64 (d, J=1.95 Hz, 1H) 13.28 (br. s., 1H); m/z=248.2 (M+1).

Workup

  1. temperatureheating
  2. temperatureAfter cooling the reaction mixture
  3. customthe resulting solids collected
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c496d5f61100496880b31db62e4f1d6d
Source dataset
uspto-grants-2014_10
Patent number
US08859577B2

Reaction notes

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