HCID 118452504, compound → HCID 118452439, compound

HRID 1773240Notes

Reaction equation

HRID 1773240 reaction equation
[CH2:1]([C:4]1[C:9]([CH3:10])=[CH:8][C:7]([N+:11]([O-])=O)=[CH:6][C:5]=1[Cl:14])[CH:2]=[CH2:3]>CO.[Ni]>[Cl:14][C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([CH3:10])[C:4]=1[CH2:1][CH2:2][CH3:3])[NH2:11]

Participants

4

Reactant 1

HCID 118452504HCID 118452504, compound

Product 1

HCID 118452439HCID 118452439, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-allyl-1-chloro-3-methyl-5-nitrobenzene (450 mg, 2.13 mmol) in 43 mL of MeOH was put on an H-cube with a Ra—Ni cartridge, the reaction was at room temperature and under 2 atm of H2 for 3 hr. The reaction was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography, 100% Heptane-15% Ethyl Acetate/85% Heptane, to give 3-chloro-5-methyl-4-propylaniline (212 mg). LCMS retention time=1.34 minutes (LC method 1); MS (m+1)=184.1. 1H NMR (400 MHz, DMSO-d6) δ 0.92 (t, J=7.3 Hz, 3H), 1.34-1.48 (m, 2H), 2.16 (s, 3H), 2.48-2.52 (m, 2H), 5.03 (s, 2H), 6.32 (d, J=1.8 Hz, 1H), 6.43 (d, J=2.2 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customThe residue was purified by silica gel flash chromatography, 100% Heptane-15% Ethyl Acetate/85% Heptane

Sources & evidence

ORD record
ord-fd4a832588a54331b1541d4cdf0e20eb
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Reaction notes

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