5-Methyl-4-nitro-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester → 5-Methyl-4-amino-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester

HRID 583771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583771
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][O:11][C:12]([C:14]3[S:15][C:16]([CH3:22])=[C:17]([N+:19]([O-])=O)[CH:18]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1>O1CCCC1.[Ni]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][O:11][C:12]([C:14]3[S:15][C:16]([CH3:22])=[C:17]([NH2:19])[CH:18]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Komponenten

4

Edukt 1

HCID 696928385-Methyl-4-nitro-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester

Produkt 1

HCID 696934745-Methyl-4-amino-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sponge nickel (0.5 g water wet) was added to a solution of 5-methyl-4-nitro-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester (0.55 g, 1.7 mmol) from Step 1 in tetrahydrofuran (100 mL) and the mixture was hydrogenated at room temperature under a hydrogen atmosphere at a starting pressure of 50 psi. After a reaction time of 2.79 hours, the pressure was released, and the mixture was filtered. The slurry was washed with tetrahydrofuran, and the filtrate was stripped of solvent under reduced pressure to afford a crystalline residue. The residue was triturated in diethyl ether and filtered to afford 5-methyl-4-amino-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester. Chromatography on silica gel in ethyl acetate, then evaporation of the effluent under reduced pressure gave 0.14 g of 5-methyl-4-amino-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester.

Aufarbeitung

  1. customwas hydrogenated at room temperature under a hydrogen atmosphere at a starting pressure of 50 psi
  2. customAfter a reaction time of 2.79 hours
  3. filtrationthe mixture was filtered
  4. washThe slurry was washed with tetrahydrofuran
  5. customto afford a crystalline residue
  6. customThe residue was triturated in diethyl ether
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-1658746fc3444c17ac4385a1807a29ad
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924276B2

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