Hydrochloric Acid → HCID 68999265, compound

HRID 1821352Notes

Reaction equation

HRID 1821352 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19](=[O:30])[C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[C:22]([CH3:29])[CH:21]=2)=[N:2]1.Cl.[Sn](Cl)Cl.[OH-].[Na+]>C(O)(=O)C>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2/[CH:11]=[CH:10]/[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:30])=[CH:21][C:22]=1[CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 68997024HCID 68997024, compound

Product 1

HCID 68999265HCID 68999265, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

Compound 157 (0.10 g, 0.25 mmol) was dissolved in acetic acid (1.0 mL) and hydrochloric acid (1.0 mL) and the solution was added with tin(II) chloride (0.10 g, 0.5 mmol), followed by stirring at 40° C. for 2 hours. Then, the reaction mixture was neutralized by adding 6 mol/L sodium hydroxide and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated in ethanol to obtain Compound 158 (46 mg, 50%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was triturated in ethanol

Sources & evidence

ORD record
ord-c45d4a4591f94d3ea0d59a4970019a0c
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

Loading…