5-Cyclopropylethynyl-3-nitrothiophene-2-carboxylic acid methyl ester → 3-Amino-5-(2-cyclopropylethyl)thiophene-2-carboxylic acid methyl ester

HRID 72211Notes

Reaction equation

HRID 72211 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13]#[C:14][CH:15]2[CH2:17][CH2:16]2)=[CH:8][C:9]=1[N+:10]([O-])=O)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:13][CH2:14][CH:15]2[CH2:16][CH2:17]2)=[CH:8][C:9]=1[NH2:10])=[O:4]

Participants

4

Reactant 1

HCID 689420965-Cyclopropylethynyl-3-nitrothiophene-2-carboxylic acid methyl ester

Product 1

HCID 689452633-Amino-5-(2-cyclopropylethyl)thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 5-cyclopropylethynyl-3-nitrothiophene-2-carboxylic acid methyl ester (1.0 g) and palladium (5% on carbon) (170 mg) in methanol (50 mL) was vigorously stirred under an atmosphere of hydrogen at atmospheric pressure for 5 h. The catalyst was then filtered off through kieselguhr, and the solvent was removed in vacuo. The product with the molecular weight of 225.31 (C11H15NO2S) was obtained in this way; MS (ESI): 226 (M+H+).

Workup

  1. filtrationThe catalyst was then filtered off through kieselguhr
  2. customthe solvent was removed in vacuo
  3. customThe product with the molecular weight of 225.31 (C11H15NO2S) was obtained in this way

Sources & evidence

ORD record
ord-b4b3cafbf26041a3bb0b59bd5835c398
Source dataset
uspto-grants-2014_09
Patent number
US08828991B2

Reaction notes

Loading…