Hydrazine hydrate (1:1) → 4-(3,3-Dimethyl-butyryl)-benzylamine

HRID 911587Notes

Reaction equation

HRID 911587 reaction equation
O.NN.[CH3:4][C:5]([CH3:28])([CH3:27])[CH2:6][C:7]([C:9]1[CH:26]=[CH:25][C:12]([CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:11][CH:10]=1)=[O:8]>CO>[CH3:4][C:5]([CH3:28])([CH3:27])[CH2:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:25][CH:26]=1)=[O:8]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 576560342-[4-(3,3-Dimethyl-butyryl)-benzyl]-isoindole-1,3-dione

Product 1

HCID 576563504-(3,3-Dimethyl-butyryl)-benzylamineYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add hydrazine hydrate (0.189 mL, 3.913 mmol) to a stirred suspension of 2-[4-(3,3-dimethyl-butyryl)-benzyl]-isoindole-1,3-dione (875 mg, 2.609 mmol) in methanol (15 mL). Heat the mixture to reflux overnight. Cool the mixture to room temperature and concentrate in vacuo. Partition the residue between EtOAc and 5N aqueous HCl and wash the acidic aqueous phase again with 5N aqueous HCl. Basify with 5N aqueous NaOH to pH 12. Extract the basic aqueous solution three times with chloroform. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to give the title compound as a yellow oil (411 mg, 77%) that was used without any further purification.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux overnight
  3. concentrationconcentrate in vacuo
  4. customPartition the residue between EtOAc and 5N aqueous HCl
  5. washwash the acidic aqueous phase again with 5N aqueous HCl
  6. extractionExtract the basic aqueous solution three times with chloroform
  7. dry with materialDry the combined organic extracts over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-e83e432ffaa347be8dc384504ae70d63
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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