Ammonia → Methyl 3-(aminomethyl)thiophene-2-carboxylate

HRID 2091562Notes

Reaction equation

HRID 2091562 reaction equation
Br[CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([O-:10])=O.[NH3:11].CN([CH:15]=[O:16])C>CO>[NH2:11][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([O:16][CH3:15])=[O:10]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 86670209HCID 86670209, compound

Product 1

HCID 53419606Methyl 3-(aminomethyl)thiophene-2-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(bromomethyl)thiophene-2-carboxylate (9.3 g, 39.6 mmol) in DMF (150 mL) was added 7.0 N NH3 in MeOH (150 mL). After stirring at room temperature for 1 h, the reaction was concentrated and purified by flash chromatography over silica gel (5%-10% MeOH/DCM) to provide methyl 3-(aminomethyl)thiophene-2-carboxylate (4.86 g, 72% yield) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.83 (d, J=5.0 Hz, 1H), 7.28 (d, J=5.0 Hz, 1H), 4.45 (s, 2H), 3.94 (s, 3H); MS (EI) m/z=172.2 [M+1]+.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified by flash chromatography over silica gel (5%-10% MeOH/DCM)

Sources & evidence

ORD record
ord-c4b4aa536230435e9190b51ee7a3a474
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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