Hydrochloric Acid → HCID 68772019, compound

HRID 1172321Notes

Reaction equation

HRID 1172321 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C@H:14]([N+:15]([O-])=O)[CH2:13][CH:12]=[CH:11][CH2:10]1.Cl.C([O-])(O)=O.[Na+]>CO.[Zn]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C@H:14]([NH2:15])[CH2:13][CH:12]=[CH:11][CH2:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68773414HCID 68773414, compound

Product 1

HCID 68772019HCID 68772019, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of Example 2A (100 mg, 0.037 mmol) in a 2 mL solution of 1:1 aqueous concentrated HCl in methanol at 0° C., Zn dust (32 mg, 0.5 mmol) was added in several portions. The solution was allowed to warm to room temperature over three hours, after which the solution was carefully basified with saturated NaHCO3. The mixture was extracted with ethyl acetate, concentrated, taken up in dichloromethane, and filtered through Celite. Concentration of the filtrate gave the title compound. 1H NMR (300 MHz, C5D5N) δ ppm 7.48 (s, 1H), 7.31-7.33 (m, 2H), 5.68-5.73 (m, 2H), 3.28-3.37 (m, 2H), 2.45-2.49 (m, 1H), 2.29-2.36 (m, 1H), 2.06-2.13 (m, 2H). MS (ESI+) m/z 243 (M+H)+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. concentrationconcentrated
  3. filtrationfiltered through Celite

Sources & evidence

ORD record
ord-9a82aab4cb8040209a2b11525de54e58
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

Loading…