Sodium Bicarbonate → ethyl 5-amino-3-methylthiophene-2-carboxylate

HRID 2067315Notes

Reaction equation

HRID 2067315 reaction equation
Cl.[NH2:2][C:3]1[S:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:13])[CH:4]=1.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:2][C:3]1[S:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:13])[CH:4]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 19100801Ethyl 5-amino-3-methylthiophene-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 2064026ethyl 5-amino-3-methylthiophene-2-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 5-amino-3-methylthiophene-2-carboxylate hydrochloride (5.80 g, 26.2 mmol) was suspended in dichloromethane (200 mL). To the suspension was added saturated aqueous sodium bicarbonate solution (250 mL). The resulting mixture was stirred for 15 minutes, then the two layers were separated. The aqueous layer was extracted with dichloromethane (100 mL). The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to afford ethyl 5-amino-3-methylthiophene-2-carboxylate (4.75 g, 98%).

Workup

  1. customthe two layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane (100 mL)
  3. dry with materialThe combined organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd89e78fa49c4d3380377d3781e175bb
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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