Methylamine → 2-Methylthiophene-3-carboxylic acid

HRID 1814503Notes

Reaction equation

HRID 1814503 reaction equation
[Cl-].[CH3:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8]([O-:10])=[O:9].C1COCC1.CN>C(OCC)(=O)C>[CH3:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 225034702-Methyl-3-thiophenecarboxylate chloride

Product 1

HCID 46254092-Methylthiophene-3-carboxylic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-3-thiophenecarboxylate chloride (60.5 g)/THF (300 ml) solution was added dropwise to a 40% aqueous solution of methylamine (400 ml) at 0° C. Ethyl acetate (2 l) was added thereto, and then the organic layer was washed sequentially with water, a 5N aqueous solution of hydrochloride acid, an aqueous solution of saturated of saturated sodium bicarbonate, water and brine, dried and evaporated. The resulting residue was crystallized from n-hexane, to give the title compound as a white powder (43.5 g, yield; 71.8%).

Workup

  1. washthe organic layer was washed sequentially with water
  2. dry with materiala 5N aqueous solution of hydrochloride acid, an aqueous solution of saturated of saturated sodium bicarbonate, water and brine, dried
  3. customevaporated
  4. customThe resulting residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-543d502e31254f8e811ab60f5ce57690
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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