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

HRID 910636Notes

Reaction equation

HRID 910636 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 an 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 phosphorous pentoxide under reduced pressure, to obtain 17.41 g (corresponding to 74.71 mmol) of 2-bromo-3-methoxy-6-nitropyridine (FIG. 5, Step 2).

Workup

  1. stirringthe mixture was stirred at room temperature for 10 minutes
  2. stirringfurther stirred for an 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 phosphorous pentoxide under reduced pressure

Sources & evidence

ORD record
ord-86a411f2ad02488a8c40f3eeb5b44cc1
Source dataset
uspto-grants-2011_09
Patent number
US08022207B2

Reaction notes

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