Thiophene → HCID 18997248, compound

HRID 374544Notes

Reaction equation

HRID 374544 reaction equation
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-])=O)[O:6][CH2:5][CH2:4][O:3]1.[O-2].[Ca+2].S1C=CC=C1>O1CCCC1.[Pt]>[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH2:13])[O:3][CH2:4][CH2:5][O:6]1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 6065442-Methyl-2-(2-nitrophenyl)-1,3-dioxolaneHCID 6850728Calciumoxide

Product 1

HCID 18997248HCID 18997248, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-methyl-2-(2-nitrophenyl)- 1,3-dioxolane (0.132 mol) was dissolved in tetrahydrofuran (600 ml) and this solution was hydrogenated with platinum on activated carbon (4 g) as a catalyst in the presence of calcium oxide (10 g) and thiophene (3 ml). After uptake of H2 (3 equiv), the catalyst was filtered on celite and washed with tetrahydrofuran. The flitrate was evaporated. The residue was recrystallized from n-hexane. The crystals were filtered off and dried, yielding 18.5g (78%) of 2-(2-methyl-1,3-dioxolan-2-yl)benzenamine (interm. 27).

Workup

  1. filtrationAfter uptake of H2 (3 equiv), the catalyst was filtered on celite
  2. washwashed with tetrahydrofuran
  3. customThe flitrate was evaporated
  4. customThe residue was recrystallized from n-hexane
  5. filtrationThe crystals were filtered off
  6. customdried

Sources & evidence

ORD record
ord-2c23ca6dc48045dfbbd97d0d4f80dd03
Source dataset
uspto-grants-1996_01
Patent number
US05480912

Reaction notes

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