Sodium Carbonate → HCID 827562, compound

HRID 73961Notes

Reaction equation

HRID 73961 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.[N+:11]([O-])([O-:13])=[O:12].[K+].C([O-])([O-])=O.[Na+].[Na+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[NH:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24434Potassium NitrateHCID 34115665-Bromoindoline

Product 1

HCID 827562HCID 827562, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 5-bromo-2,3-dihydro-1H-indole (45 g, 0.227 mol) in H2SO4 (98%, 200 mL) was slowly added KNO3 (23.5 g, 0.23 mol) at 0° C. After addition, the mixture was stirred at 0-10° C. for 4 h, carefully poured into ice, basified with Na2CO3 to pH 8 and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by column chromatography on silica gel to give 5-bromo-6-nitro-2,3-dihydro-1H-indole (42 g, 76%).

Workup

  1. customat 0° C
  2. additionAfter addition
  3. additioncarefully poured into ice
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c29c6924eefb4088ada82cb1a44396db
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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