1-Nitro-4-tert-butyl-2,6-dimethylbenzene → 4-Tert-butyl-2,6-dimethylaniline

HRID 12016Notes

Reaction equation

HRID 12016 reaction equation
[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][C:5]=1[CH3:15])([O-])=O.[Cl-].[Cl-].[Ca+2]>C(O)C.O.[Zn]>[CH3:15][C:5]1[CH:6]=[C:7]([C:11]([CH3:13])([CH3:12])[CH3:14])[CH:8]=[C:9]([CH3:10])[C:4]=1[NH2:1]

Participants

6

Reactant 2

HCID 2233901-Nitro-4-tert-butyl-2,6-dimethylbenzene2×HCID 5284359Calcium Chloride

Product 1

HCID 12296974-Tert-butyl-2,6-dimethylanilineYield 93.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

Water, 20 mL, was added to a mixture of 12.0 g (58.0 mmol) of 1-nitro-4-tert-butyl-2,6-dimethylbenzene dissolved in 160 mL of ethanol. To the stirring solution of 1-nitro-4-tert-butyl-2,6-dimethylbenzene was added CaCl2, 4.8 g (43.2 mmol), dissolved in 20 mL of water, followed by the addition of zinc powder, 50.0 g (76.5 mmol). The reaction was stirred overnight at 65° C., then cooled to ambient temperature and filtered. The filtrate was extracted three times with ether, and the organic layer was dried over MgSO4. Removal of the solvent gave 9.58 g (93%) of a brown oil. 1H NMR (300 MHz, CDCl3): δ=6.90, s, 2H; 3.40, broad singlet, 2H; 2.11, s, 6H, 1.21, s, 9H.

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationfiltered
  3. extractionThe filtrate was extracted three times with ether
  4. dry with materialthe organic layer was dried over MgSO4
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-3ae22f97cb3a4f52b62b49ef8cde42a7
Source dataset
uspto-grants-2010_06
Patent number
US07727926B2

Reaction notes

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