Sodium Bicarbonate → HCID 68773399, compound

HRID 1172323Notes

Reaction equation

HRID 1172323 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F: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.C([O-])(O)=O.[Na+]>Cl.CO.[Zn]>[Cl:1][C:2]1[CH:7]=[C:6]([F: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 2

HCID 516892Sodium BicarbonateHCID 68770669HCID 68770669, compound

Product 1

HCID 68773399HCID 68773399, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of Example 3A (100 mg, 0.039 mmol) in 2 mL 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 7.33-7.35 (m, 1H), 7.22-7.28 (m, 1H), 7.06-7.10 (m, 1H), 5.68-5.77 (m, 2H), 3.22-3.37 (m, 2H), 2.43-2.48 (m, 1H), 2.29-2.36 (m, 1H), 2.06-2.14 (m, 2H). MS (ESI+) m/z 227 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-d1f342b4c9f841bebe836d410c79b88d
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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