4-Bromo-2-nitrophenylacetic Acid → 6-bromo-2,3-dihydro-1H-indol-2-one

HRID 1387413Notes

Reaction equation

HRID 1387413 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](O)=[O:10])=[C:4]([N+:12]([O-])=O)[CH:3]=1>S(=O)(=O)(O)O.C(O)C.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][C:9](=[O:10])[NH:12]2)=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 2715514-Bromo-2-nitrophenylacetic Acid

Product 1

HCID 27732896-bromo-2,3-dihydro-1H-indol-2-one

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

Zinc dust (8.5 g, 0.13 mol) was added slowly to a solution of 4-bromo-2-nitrophenylacetic acid (8.4 g, 0.03 mol) in 50% sulfuric acid (200 mL) and absolute ethanol (300 mL) at 90° C. over 0.75 h. The mixture was heated at this temperature for 2 h with stirring. The excess ethanol was removed by evaporation in vacuo and the mixture was filtered. The filtrate was extracted with diethyl ether. The combined organic portions were washed with saturated sodium bicarbonate, saturated sodium chloride, filtered with Whatman 1 PS Phase Separator paper and evaporated in vacuo to give 3.8 g (56%) a pale peach solid. 1H-NMR (DMSO-d6): δ10.57 (brs, 1H), 7.14 (m, 2H), 6.98 (s, 1H), 3.47 (s, 2H).

Workup

  1. temperatureThe mixture was heated at this temperature for 2 h
  2. customThe excess ethanol was removed by evaporation in vacuo
  3. filtrationthe mixture was filtered
  4. extractionThe filtrate was extracted with diethyl ether
  5. washThe combined organic portions were washed with saturated sodium bicarbonate, saturated sodium chloride
  6. filtrationfiltered with Whatman 1 PS Phase Separator paper
  7. customevaporated in vacuo
  8. customto give 3.8 g (56%) a pale peach solid

Sources & evidence

ORD record
ord-0a97abfee5d0427d9fa01caebfba961c
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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