4-Methyl-5-(3-nitrophenyl)-1,3-oxazole → 3-(4-Methyl-1,3-oxazol-5-yl)aniline

HRID 1157616Notes

Reaction equation

HRID 1157616 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1>CO.[Pd]>[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[NH2:13]

Participants

4

Reactant 1

HCID 595136834-Methyl-5-(3-nitrophenyl)-1,3-oxazole

Product 1

HCID 595114203-(4-Methyl-1,3-oxazol-5-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (5 g) was transferred carefully to a solution of 4-methyl-5-(3-nitrophenyl)-1,3-oxazole (50 g) in MeOH (600 mL) in a Parr-shaker bottle and hydrogenated at 3.5 kg pressure for 20 h. The reaction mixture was filtered over a celite bed and the filtrate concentrated. The residue was purified by silica gel column chromatograph using 40% EtOAc in petroleum-ether to get a yellow solid. Yield 18 g (42%). 1H NMR (400 MHz, DMSO-d6) δ 8.23 (s, 1H), 7.08 (t, J=8.0 Hz, 1H), 6.82 (s, 1H), 6.71 (d, J=7.9 Hz, 1H), 6.52 (d, J=8.2 Hz, 1H), 5.24 (s, 2H), 2.29 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered over a celite bed
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified by silica gel column chromatograph
  4. customto get a yellow solid

Sources & evidence

ORD record
ord-94e852a306e34dfcb45c72111614aa3e
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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