Methyl iodide → 3-Methyl-4-methylamino-benzofuran-2-carboxylic acid ethyl ester

HRID 29302Notes

Reaction equation

HRID 29302 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].IC.[C:19](=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][CH3:19])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 687122774-Amino-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687132403-Methyl-4-methylamino-benzofuran-2-carboxylic acid ethyl esterYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4-amino-3-methyl-benzofuran-2-carboxylic acid ethyl ester (500 mg, 2.28 mmol, 1 eq.) was added iodomethane (310 uL, 6.16 mmol, 2.7 eq.), sodium carbonate (314 mg, 2.96 mmol, 1.3 eq.), and ethanol (10 mL) and reaction was heated at reflux for 16 hours. 3-Methyl-4-methylamino-benzofuran-2-carboxylic acid ethyl ester was obtained in 17% yield after flash column chromatography, eluting with ethyl acetate/hexanes. (90 mg) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.3 (t, J=7.1 Hz, 3 H) 2.7 (s, 3 H) 4.3 (q, J=7.1 Hz, 2 H) 6.5 (dd, J=7.8, 0.8 Hz, 1 H) 6.8 (d, J=8.3 Hz, 1 H) 7.2 (t, J=8.1 Hz, 1 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours

Sources & evidence

ORD record
ord-a38411db4a67416083bb77185f55c1e5
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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