Hydrochloric Acid → HCID 118108336, compound

HRID 2174523Notes

Reaction equation

HRID 2174523 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([OH:14])=[O:13])=[CH:6]2.Cl.[CH2:16](O)[CH2:17][CH3:18]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:16][CH2:17][CH3:18])=[O:13])=[CH:6]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10311-PropanolHCID 204015-Methoxyindole-2-carboxylic acid

Product 1

HCID 118108336HCID 118108336, compoundYield 88%

Procedure

To a suspension of 300 (670 mg, 3.50 mmol) in anhydrous n-PrOH (20 mL) was added HCl (4 N in dioxane, 2.5 mL). The reaction mixture was heated at reflux for 36 h. Upon completion, volatiles were evaporated in vacuo and the resulting oil was purified by chromatography (0% to 20% EtOAc/hexanes) to produce a white powder (721 mg, 88%): mp 104-107° C. TLC Rf 0.51 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3) δ 8.82 (s, 1H), 7.32-7.31 (d, 1H, J=8.94 Hz), 7.15 (m, 1H), 7.08 (d, 1H, J=2.4 Hz), 7.01-6.99 (dd, 1H, J1=8.94 Hz, J2=2.46 Hz), 4.32-4.29 (t, 2H, J=6.72 Hz), 3.85 (s, 3H), 1.84-1.78 (sex, 2H, J=7.38 Hz), 1.05-1.03 (t, 3H, J=7.38 Hz). 13C NMR (150 MHz, CDCl3) δ 162.0, 154.7, 132.1, 127.88, 127.85, 117.0, 112.7, 108.2, 102.5, 66.5, 55.7, 22.2, 10.5. Elemental analysis calculated for C13H15NO3: C, 66.94; H, 6.48; N, 6.00. Found: C, 66.87; H, 6.44; N; 6.00.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 36 h
  3. customUpon completion, volatiles were evaporated in vacuo
  4. customthe resulting oil was purified by chromatography (0% to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b88a6022a3a4434ca3ccbc8b95a98012
Source dataset
uspto-grants-2015_06
Patent number
US09061994B1

Reaction notes

Loading…