Sodium hydride → Methyl 3-amino-1-benzofuran-2-carboxylate

HRID 1358301Notes

Reaction equation

HRID 1358301 reaction equation
[C:1]([C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])#[N:2].[H-].[Na+]>CS(C)=O>[NH2:2][C:1]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[O:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 1472933Methyl 2-(2-cyanophenoxy)acetate

Product 1

HCID 674268Methyl 3-amino-1-benzofuran-2-carboxylateYield 56.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of methyl 2-(2-cyanophenoxy)ethanoate (3.82 g, 20 mmol) in DMSO (40 mL) is added dropwise to a suspension of NaH (0.84 g, 21 mmol) and DMSO (10 mL) stirred under N2 at 25° C. After 10 min the mixture is poured onto ice water and extracted with ether. The combined extracts are washed with water, saturated brine and dried (MgSO4). After removal of the solvent under reduced pressure, methyl 3-aminobenzo[b]furan-2-carboxylate (2.15 g, 56%) is obtained as a yellow solid. 1H NMR (DMSO) δ7.95 (1H, d, J=7.7 Hz), 7.48 (2H, d, J=3.4 Hz), 7.29-7.22 (1H, m), 6.40 (2H, brs), 3.80 (3H, s).

Workup

  1. additionAfter 10 min the mixture is poured onto ice water
  2. extractionextracted with ether
  3. washThe combined extracts are washed with water, saturated brine
  4. dry with materialdried (MgSO4)
  5. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-f3813dba87ce4208832fd6959cd94ce6
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

Loading…