Hydrazine hydrate (1:1) → HCID 67367864, compound

HRID 1927640Notes

Reaction equation

HRID 1927640 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][C:22]=1[Cl:23])[O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([N+:16]([O-])=O)=[C:11]([CH3:19])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)CC.[Pd]>[C:1]([C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][C:22]=1[Cl:23])[O:8][C:9]1[CH:10]=[C:11]([CH3:19])[C:12](=[CH:13][C:14]=1[CH3:15])[NH2:16])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67369357HCID 67369357, compound

Product 1

HCID 67367864HCID 67367864, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 10311-PropanolSolvent

Procedure

A solution of 40 g (119 mmol) of 4-(3-t-butyl-4-chlorphenoxy)-2,5-dimethylnitrobenzene in 30 ml of n-propanol was treated dropwise with hydrazine hydrate (17.3 ml, 356 mmol), then Pd/C was added (5% on charcoal, 400 mg, 0.2 mmol of Pd) and the mixture was heated to reflux for 10 hrs. After cooling to room temperature the mixture was filtrated, the residue was washed with methanol and the combined filtrates were evaporated. The residue was dissolved in dichloromethane, and the solution was extracted several times with water in order to remove remaining n-propanol. The organic phase was dried over Na2SO4, filtrated and evaporated. Yield: 32 g (87%); log P (pH 2.3)=4.38.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 10 hrs
  3. filtrationwas filtrated
  4. washthe residue was washed with methanol
  5. customthe combined filtrates were evaporated
  6. dissolutionThe residue was dissolved in dichloromethane
  7. extractionthe solution was extracted several times with water in order
  8. customto remove
  9. dry with materialThe organic phase was dried over Na2SO4
  10. filtrationfiltrated
  11. customevaporated

Sources & evidence

ORD record
ord-712b8193d4e14530846715fa95d9ad37
Source dataset
uspto-grants-2012_05
Patent number
US08183296B2

Reaction notes

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