Hydrochloric Acid → HCID 69004339, compound

HRID 1821407Notes

Reaction equation

HRID 1821407 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]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][OH:26])[CH2:20][CH2:19]3)=[CH:14][C:13]=2[N+:27]([O-])=O)=[N:2]1.[Sn].Cl.[OH-].[Na+]>C(O)C>[NH2:27][C:13]1[CH:14]=[C:15]([N:18]2[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][OH:26])[CH2:22][CH2:23]2)[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 69002947HCID 69002947, compound

Product 1

HCID 69004339HCID 69004339, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

(E)-2-(4-{4-[2-(1H-indazol-3-yl)vinyl]-3-nitrophenyl}piperazin-1-yl)ethanol (0.26 g, 0.66 mmol) obtained in Step 2 was dissolved in ethanol (3.0 mL), and the solution was added with tin (0.17 g, 1.4 mmol) and concentrated hydrochloric acid (1.5 mL) under ice-cooling, followed by stirring at 40° C. for 1 hour. To the reaction mixture under ice-cooling, 6 mol/L aqueous sodium hydroxide solution was added to neutralize the mixture. 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 to obtain (E)-2-(4-{3-amino-4-[2-(1H-indazol-3-yl)vinyl]phenyl}piperazin-1-yl)ethanol (0.24 g, 100%).

Workup

  1. temperaturecooling
  2. temperatureTo the reaction mixture under ice-cooling
  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

Sources & evidence

ORD record
ord-7f9ec4a04c0a4738b7d13fa12272b7bc
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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