Ammonia → HCID 53968927, compound

HRID 1773226Notes

Reaction equation

HRID 1773226 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](OCC)=[O:11])=[CH:7][C:6]=2[CH:15]=1.[NH3:16]>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH2:16])=[O:11])=[CH:7][C:6]=2[CH:15]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13157013Ethyl 5-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 53968927HCID 53968927, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 5-methylbenzofuran-2-carboxylate, (1.19 g, 5.83 mmol) was suspended in 20 ml of 7M NH3 in MeOH. The mixture was stirred at 50° C. in a sealed tube overnight. After cooling to room temperature, the solvent was evaporated under reduced pressure to give pure 5-methylbenzofuran-2-carboxamide, as a white solid (1.02 g). LCMS retention time=1.00 minutes (LC method 3); MS (m+1)=175.8. 1H NMR (400 MHz, DMSO-d6) δ 2.40 (s, 3H), 7.45 (d, J=0.9 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.53 (t, J=0.7 Hz, 1H), 7.63 (br. s., 1H), 8.05 (br. s., 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6efddbc6e6ec4f4396f932bc7edbabb1
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Reaction notes

Loading…