4-Bromo-2-nitro-cyclopropylbenzene → Tranylcypromine

HRID 725832Notes

Reaction equation

HRID 725832 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH:9]2[N+:11]([O-])=O)=[CH:4][CH:3]=1>C(O)C.[Pd]>[NH2:11][CH:9]1[CH2:10][CH:8]1[C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 539104494-Bromo-2-nitro-cyclopropylbenzene

Product 1

HCID 5530Tranylcypromine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3.5 g of 4-bromo-2-nitro-cyclopropylbenzene are dissolved in 30 ml of ethanol and, after addition of 0.5 g of palladium-on-charcoal (10%), are hydrogenated in a Parr apparatus at room temperature under a hydrogen pressure of 5 bar for 2.5 hours. After cooling, the solvent is distilled off in a rotary evaporator and the residue is rendered alkaline with 1N sodium hydroxide solution and extracted three times with 50 ml of ether each time. The combined organic phases are dried over sodium sulphate, the solvent is distilled off in a rotary evaporator and the residue is purified by column chromatography.

Workup

  1. customare hydrogenated in a Parr apparatus at room temperature under a hydrogen
  2. customfor 2.5 hours
  3. temperatureAfter cooling
  4. distillationthe solvent is distilled off in a rotary evaporator
  5. extractionextracted three times with 50 ml of ether each time
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. distillationthe solvent is distilled off in a rotary evaporator
  8. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-d9f7ea18dee34b04aa88c425d1b95bf5
Source dataset
uspto-grants-1998_01
Patent number
US05707989

Reaction notes

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