Sulfuric Acid → HCID 15645653, compound

HRID 1294065Notes

Reaction equation

HRID 1294065 reaction equation
[OH:1]S(O)(=O)=O.[Br:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=1.[NH4+:19].[OH-:20]>>[Br:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10]([N+:9]([O-:1])=[O:20])=[N:19][CH:8]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 2823185HCID 2823185, compound

Product 1

HCID 15645653HCID 15645653, compoundYield 54%

Conditions

Temperature
0 °C

Procedure

To a mixture of concentrated H2SO4 (3.0 mL) and fHNO3 (2.1 mL), 3-bromo-5-(ethoxycarbonyl)aminopyridine (Intermediate 9–20.0 g, 99.0 mmol) was portionwise added at 0° C. After stirring at 0° C. for 5 min., the mixture was stirred at room temperature overnight. The mixture was poured into ice-water then basified with aqueous NH4OH. The mixture was extracted with ethyl acetate. The organic layer was washed with aqueous NH4OH and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave 5-bromo-3-(ethoxycarbonyl)amino-2-nitropyridine (1.57 g, 54%).

Workup

  1. additionwas portionwise added at 0° C
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with aqueous NH4OH and brine
  5. dry with materialdried over Na2SO4
  6. customthen evaporated
  7. customSequence purification on SiO2 column chromatography

Sources & evidence

ORD record
ord-7121a27874f148af885713bb62102197
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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