Methanol → Methyl 4-amino-5-methylthiophene-2-carboxylate

HRID 453569Notes

Reaction equation

HRID 453569 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[N+:11]([O-])=O.CO>O1CCCC1.[C].[Pd]>[NH2:11][C:3]1[CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[S:6][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 887MethanolHCID 268679Methyl 5-methyl-4-nitrothiophene-2-carboxylate

Product 1

HCID 59640747Methyl 4-amino-5-methylthiophene-2-carboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 5-methyl-4-nitrothiophene-2-carboxylate (95 g) and 10% palladium-carbon (50% containing water, 10 g) in tetrahydrofuran (250 mL)-methanol (250 mL) was stirred at 50° C. for 8 hr under a hydrogen atmosphere (0.3 MPa). The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was crystallized from diethyl ether to give methyl 4-amino-5-methylthiophene-2-carboxylate (58 g, yield 72%) as yellow crystals. melting point 91° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-512b4dafb3d34000bf9a2a84d668fc87
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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