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

HRID 2059502Notes

Reaction equation

HRID 2059502 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

262 mL of conc. sulfuric acid was cooled down to −2° C., and 262 mL of 90% nitric acid was carefully added thereto. Subsequently, 65.3 g (corresponding to 0.347 mmol) of 2-bromo-3-methoxypyridine was carefully added thereto. After the reaction mixture was stirred in an ice bath for 10 minutes, the mixture was stirred at room temperature for 30 minutes, and then was heated to 55° C. and further stirred for 1.5 hours. 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 55.7 g (corresponding to 0.239 mol) of 2-bromo-3-methoxy-6-nitropyridine (FIG. 2, Step 2).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. stirringfurther stirred for 1.5 hours
  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-e01d28c665d74cf5a8ab6e0490de8460
Source dataset
uspto-grants-2012_10
Patent number
US08277777B2

Reaction notes

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