4-Bromo-7-hydroxy-6-nitro-2,3-dihydro-1H-inden-1-one → 6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-one hydrobromide

HRID 883187Notes

Reaction equation

HRID 883187 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([OH:14])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:15]>CO.[C].[Pd]>[BrH:1].[NH2:11][C:9]1[C:8]([OH:14])=[C:7]2[C:3]([CH2:4][CH2:5][C:6]2=[O:15])=[CH:2][CH:10]=1

Participants

4

Reactant 1

HCID 577812334-Bromo-7-hydroxy-6-nitro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 673534616-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-one hydrobromideYield 80%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

4-Bromo-7-hydroxy-6-nitroindan-1-one (2.90 g, 10.66 mmol) was dissolved in methanol (53 mL), a 10% palladium-carbon powder (290 mg) was added, and the mixture was stirred at room temperature for 6 hr under a hydrogen atmosphere. The catalyst was filtered off using celite, and the filtrate was concentrated under reduced pressure to give the title compound (2.08 g, yield 80%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-860343830cc2424798b24cba447395bf
Source dataset
uspto-grants-2012_08
Patent number
US08236837B2

Reaction notes

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