2-Norbornene → Methyl 4-(2-aminoanilino)thiophene-3-carboxylate

HRID 1764287Notes

Reaction equation

HRID 1764287 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[NH:4][C:5]1[CH2:6][S:7][CH2:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11].C12CC(CC1)=CC=2.C12CC(CC1)C=C2>[Pd].C1CCCCC=1>[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[NH:4][C:5]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][S:7][CH:6]=1

Participants

6

Reactant 3

HCID 103522-NorborneneHCID 2819686Methyl 4-(2-aminoanilino)-2,5-dihydrothiophene-3-carboxylateHCID 18006658Norborna-diene

Product 1

HCID 12658694Methyl 4-(2-aminoanilino)thiophene-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8079CyclohexeneSolvent

Procedure

Methyl 3-(2-aminoanilino)-2,5-dihydrothiophene-4-carboxylate (2.5 g, 0.001 mol) was added to a flask containing palladium on charcoal catalyst (5%, 200 mg) in cyclohexene (or norbornadiene or norbornylene) (50 ml) and the reaction was heated at reflux with stirring for 4 hours, the reaction being followed by t.l.c.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux

Sources & evidence

ORD record
ord-e6321cf8d8fc4077adda7bce67ed3c13
Source dataset
uspto-grants-1978_09
Patent number
US04115574

Reaction notes

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