Potassium Carbonate → ethyl 3-amino-5-chlorobenzofuran-2-carboxylate

HRID 2102830Notes

Reaction equation

HRID 2102830 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[C:14]#[N:15])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:5]1[O:6][C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[C:14]=1[NH2:15])=[O:16])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 847306HCID 847306, compound

Product 1

HCID 617363ethyl 3-amino-5-chlorobenzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-chloro-2-cyano-phenoxy)-acetic acid ethyl ester (15.3 g, 64.0 mmol) in DMF (150 mL) was added K2CO3 (14.1 g, 102 mmol). After heating at reflux for 10 h, the reaction mixture was poured into ice water. The crude product was collected by filtration as a brown solid (14.37 g, 92%). 1H NMR (CDCl3): 7.54 (s, 1H), 7.41-7.27 (m, 2H), 4.94 (s, 2H), 4.44 (q, J=7.1 Hz, 2H), 1.44 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 10 h
  3. filtrationThe crude product was collected by filtration as a brown solid (14.37 g, 92%)

Sources & evidence

ORD record
ord-efb909c2b84d4715babfe00d4f6d7771
Source dataset
uspto-grants-2009_08
Patent number
US07576092B2

Reaction notes

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