Thiophene → HCID 18997248, compound

HRID 1654544Notes

Reaction equation

HRID 1654544 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 (0.132mol) 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 tiltrate was evaporated. The residue was recrystallized from n-hexane. The crystals were filtered off and dried, yielding 18.5 g (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 tiltrate was evaporated
  4. customThe residue was recrystallized from n-hexane
  5. filtrationThe crystals were filtered off
  6. customdried

Sources & evidence

ORD record
ord-12f0d728be0b443baabdacab10175290
Source dataset
uspto-grants-1995_04
Patent number
US05407961

Reaction notes

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