Hydrochloric Acid → HCID 68999740, compound

HRID 1821333Notes

Reaction equation

HRID 1821333 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][C:15]([NH:18][C:19]([N:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:29])[CH3:28])[CH2:23][CH2:22]3)=[O:20])=[CH:14][C:13]=2[N+:30]([O-])=O)=[N:2]1.[Sn].Cl.[OH-].[Na+]>C(O)C>[NH2:30][C:13]1[CH:14]=[C:15]([NH:18][C:19]([N:21]2[CH2:26][CH2:25][N:24]([C:27](=[O:29])[CH3:28])[CH2:23][CH2:22]2)=[O:20])[CH:16]=[CH:17][C:12]=1/[CH:11]=[CH:10]/[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 68999516HCID 68999516, compound

Product 1

HCID 68999740HCID 68999740, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Compound 86 (150 mg, 0.36 mmol) was dissolved in ethanol (2 mL), and the solution was added with tin (92 mg, 0.77 mmol) and concentrated hydrochloric acid (1.0 mL) under ice-cooling, followed by stirring at 40° C. for 1 hour. To the reaction mixture, 6 mol/L sodium hydroxide was added to neutralize the mixture under ice-cooling. Then, the mixture was filtered. The filtrate was added with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated in ethyl acetate/methanol(4/1) to obtain Compound 87 (110 mg, 79%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationThen, the mixture was filtered
  4. additionThe filtrate was added with saturated aqueous sodium hydrogencarbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was triturated in ethyl acetate/methanol(4/1)

Sources & evidence

ORD record
ord-2e074ce8371e4e55a7d8aeff246510a5
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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