Hydrazine hydrate (1:1) → 2-(4-aminomethyl-3-bromophenyl)-4-(3,5-dichlorophenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrole

HRID 2386159Notes

Reaction equation

HRID 2386159 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[CH2:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[CH2:25][N:26]1C(=O)C2=CC=CC=C2C1=O.O.NN>C(O)C>[NH2:26][CH2:25][C:3]1[CH:4]=[CH:5][C:6]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:14])[F:15])[CH2:10][N:9]=2)=[CH:7][C:2]=1[Br:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86648071N-[2-bromo-4-[4-(3,5-dichlorophenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrole-2-yl]phenylmethyl]phthalimide

Product 1

HCID 580921092-(4-aminomethyl-3-bromophenyl)-4-(3,5-dichlorophenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.22 g of N-[2-bromo-4-[4-(3,5-dichlorophenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrole-2-yl]phenylmethyl]phthalimide in 5 mL of ethanol, 0.074 g of hydrazine monohydrate was added and the resultant reaction mixture was stirred while heating the mixture to reflux for 2 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and deposited insoluble substances were filtered off, followed by distilling off the solvent under reduced pressure. To the resultant residue, 20 mL of chloroform was added and insoluble substances were filtered off, followed by washing the filtrate with water (20 mL×1). Subsequently, the filtrate was dehydrated and dried over a saturated brine and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure to obtain 0.18 g of the objective substance as a yellow resinoid.

Workup

  1. customthe resultant reaction mixture
  2. temperaturewhile heating the mixture
  3. temperatureto reflux for 2 hours
  4. customAfter the completion of the reaction
  5. waitthe reaction mixture was left
  6. filtrationwere filtered off
  7. distillationby distilling off the solvent under reduced pressure
  8. additionTo the resultant residue, 20 mL of chloroform was added
  9. filtrationinsoluble substances were filtered off
  10. washby washing the filtrate with water (20 mL×1)
  11. dry with materialdried over a saturated brine and anhydrous sodium sulfate in this order
  12. distillationthe solvent was distilled off under reduced pressure
  13. customto obtain 0.18 g of the objective substance as a yellow resinoid

Sources & evidence

ORD record
ord-de24336124624d76ab38d253e01864ff
Source dataset
uspto-grants-2012_09
Patent number
US08268754B2

Reaction notes

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