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

HRID 1660919Notes

Reaction equation

HRID 1660919 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-e0a8b071296141eea2e97784c25a7c37
Source dataset
uspto-grants-2011_10
Patent number
US08030321B2

Reaction notes

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