HCID 19046449, compound → HCID 19046432, compound

HRID 1781958Notes

Reaction equation

HRID 1781958 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([CH2:12]SC)[C:8]([NH2:9])=[C:7]([Cl:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[CH:11]=[C:10]([CH3:12])[C:8]([NH2:9])=[C:7]([Cl:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 19046449HCID 19046449, compound

Product 1

HCID 19046432HCID 19046432, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4-t-Butyl-2-chloro-6-(methylthiomethyl)aniline (1.3 g) was dissolved in methanol (50 ml) and Raney-nickel (prewashed to pH 7) was added portionwise until t.l.c. indicated all starting material had reacted (ether-hexane, 1:10). The Raney-nickel was removed by filtration through Celite and the filtrate was evaporated. The residue was dissolved in ether and washed with brine, dried (MgSO4) and evaporated. The residue was purified on silica using hexane and 5% ether in hexane as eluent to afford 4-t-butyl-2-chloro-6-methylaniline as a yellow liquid. 1H NMR (360 MHz, CDCl3) δ1.26 (9H, s, (CH3)3), 2.19 (3H, s, CH3), 3.97 (2H, s, NH2), 6.97 (1H, d, J=2.0 Hz, ArH), 7.14 (1H, d, J=2.0 Hz, ArH).

Workup

  1. customThe Raney-nickel was removed by filtration through Celite
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified on silica

Sources & evidence

ORD record
ord-2dbe524b12974d9382613c2ccfb3e4d0
Source dataset
uspto-grants-1997_05
Patent number
US05633281

Reaction notes

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