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

HRID 1159980Notes

Reaction equation

HRID 1159980 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-])=O.[CH3:10][OH:11]>[Pd]>[CH3:9][C:4]1[N:1]=[CH:10][O:11][C:5]=1[C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1]

Participants

4

Reactant 2

HCID 887MethanolHCID 7416Nitrobenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of the nitrobenzene adduct (50 g) produced in the previous step C in MeOH (600 mL) was prepared in parr-shaker bottle; Pd/C (5 g) was transferred carefully and hydrogenated at 3.5 kg pressure for 20 h. The reaction mixture was filtered over celite bed and the filtrate was concentrated. The residue was purified by silica gel column chromatograph using 40% EtOAc in pet.ether to get yellow color 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. customwas prepared in parr-shaker bottle
  2. filtrationThe reaction mixture was filtered over celite bed
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatograph
  5. customether to get yellow color solid

Sources & evidence

ORD record
ord-e0c4af5ec17a4dab84861251ac12112b
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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