4-Tert-butyl-1-methyl-2-nitrobenzene → 5-tert-Butyl-2-methylaniline

HRID 1003871Notes

Reaction equation

HRID 1003871 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N+:12]([O-])=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([NH2:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 109544154-Tert-butyl-1-methyl-2-nitrobenzene

Product 1

HCID 130899795-tert-Butyl-2-methylaniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

A solution of (239 g, 1.2 mol) 4-tert-butyl-1-methyl-2-nitro-benzene (M. S. Carpenter, W. M. Easter, T. F. Wood, J. Org. Chem. (1951), 586) in MeOH (1.0 L) was treated with Raney nickel (25 g) in a Parr shaker. The apparatus was sealed under hydrogen pressure to 52 psi, heated to 35° C. for 15 hours, and cooled to room temperature. The apparatus was vented and the contents filtered. The filtrate was concentrated in vacuo and distilled, collecting the major fraction (75-85° C., 1.0 torr). 1H NMR (CDCl3) δ 1.26 (s, 9 H), 2.11 (s, 3 H), 3.54 (bs, 2 H), 6.69 (d, 1 H), 6.72 (dd, 1 H), 6.96 (d, 1 H).

Workup

  1. customThe apparatus was sealed under hydrogen pressure to 52 psi
  2. temperaturecooled to room temperature
  3. filtrationthe contents filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. distillationdistilled
  6. customcollecting the major fraction (75-85° C., 1.0 torr)

Sources & evidence

ORD record
ord-949ed18d9dc64b87b85978c5bca867ee
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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