Nitric Acid → 2-Bromo-3-methoxy-6-nitropyridine

HRID 2059507Notes

Reaction equation

HRID 2059507 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[Br:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][N:12]=1>>[Br:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([N+:6]([O-:9])=[O:7])[N:12]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 903642-Bromo-3-methoxypyridine

Product 1

HCID 126928732-Bromo-3-methoxy-6-nitropyridine

Conditions

Temperature
55 °C

Procedure

83 mL of conc. sulfuric acid was cooled down to −5° C., and 83 mL of 90% nitric acid was carefully added thereto. Subsequently, 20.69 g (corresponding to 110.04 mmol) of 2-bromo-3-methoxypyridine was carefully added thereto. After the reaction mixture was stirred in an ice bath for 5 minutes, the mixture was stirred at room temperature for 10 minutes, and then was heated to 55° C. and further stirred for one hour. After the reaction solution was cooled to room temperature, the reaction solution was poured little by little into crushed ice to generate precipitates. The precipitates were filtered and washed with water, and then dried over phosphorus pentaoxide under reduced pressure, to obtain 17.41 g (corresponding to 74.71 mmol) of 2-bromo-3-methoxy-6-nitropyridine (FIG. 3, Step 2).

Workup

  1. stirringthe mixture was stirred at room temperature for 10 minutes
  2. stirringfurther stirred for one hour
  3. temperatureAfter the reaction solution was cooled to room temperature
  4. additionthe reaction solution was poured little by little
  5. custominto crushed ice
  6. customto generate precipitates
  7. filtrationThe precipitates were filtered
  8. washwashed with water
  9. dry with materialdried over phosphorus pentaoxide under reduced pressure

Sources & evidence

ORD record
ord-607571f9c2a748aca1fa898a338aef5f
Source dataset
uspto-grants-2012_10
Patent number
US08277777B2

Reaction notes

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