4,4-Dimethyl-2-(2-methyl-3-nitrophenyl)-4,5-dihydro-1,3-oxazole → HCID 14407618, compound

HRID 621462Notes

Reaction equation

HRID 621462 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[C:8]=2[CH3:16])=[N:3]1.[H][H]>O1CCCC1.[Pd]>[CH3:1][C:2]1([CH3:17])[CH2:6][O:5][C:4]([C:7]2[C:8]([CH3:16])=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=2)=[N:3]1

Participants

5

Reactant 2

HCID 7993934,4-Dimethyl-2-(2-methyl-3-nitrophenyl)-4,5-dihydro-1,3-oxazoleHCID 178418361HCID 178418361, compound2×

Product 1

HCID 14407618HCID 14407618, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 29.82 g of 4,5-dihydro-4,4-dimethyl-2-(2-methyl-3-nitrophenyl)oxazole in 500 ml of tetrahydrofuran is added 0.5 g of 10% palladium on barium sulfate. The mixture is exposed to hydrogen gas until the appropriate quantity of hydrogen is taken up, filtered and the solvent evaporated to give 24.7 g of 3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-2-methylbenzenamine as a gum which crystallizes on cooling; mp 45° C.

Workup

  1. filtrationfiltered
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-e2e91642958d4876a5fcabd955a68f0c
Source dataset
uspto-grants-1989_04
Patent number
US04824843

Reaction notes

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