N-Methoxy-N-methylbenzofuran-5-carboxamide → 2,3-Dihydro-benzofuran-5-carboxylic acid methoxy-methyl-amide

HRID 1671361Notes

Reaction equation

HRID 1671361 reaction equation
[CH3:1][O:2][N:3]([CH3:15])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]=[CH:11][C:10]=2[CH:14]=1)=[O:5]>C(O)C.[Pd]>[CH3:1][O:2][N:3]([CH3:15])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH2:12][CH2:11][C:10]=2[CH:14]=1)=[O:5]

Participants

4

Reactant 1

HCID 59186071N-Methoxy-N-methylbenzofuran-5-carboxamide2×

Product 1

HCID 591860532,3-Dihydro-benzofuran-5-carboxylic acid methoxy-methyl-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of benzofuran-5-carboxylic acid methoxy-methyl-amide (Intermediate P, 235 mg, 1.145 mmol) in ethanol (20 ml) is hydrogenated over 10% Pd on carbon (30×4 mm CatCart®) at 40° C. and 30 bar using the H-Cube Hydrogenator. After 6 hrs the reaction is complete and the reaction mixture is concentrated in vacuo to give an oil; MS m/z=208.1 [M+H]+; H NMR 400.13 MHz (CDCl3)-7.6 (1H, s), 7.55 (1H, d), 7.8 (1H, d), 4.6 (2H, t), 3.6 (3H, s), 3.35 (3H, s), 3.25 (2H, t).

Workup

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. customto give an oil

Sources & evidence

ORD record
ord-680530ea05b944198daa0e1529f19d67
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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