Sodium Bicarbonate → HCID 19067154, compound

HRID 481778Notes

Reaction equation

HRID 481778 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH:7]([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([N+:19]([O-])=O)=[CH:14][CH:15]=2)[CH2:10]1)[CH3:8])=[O:5])[CH3:2].O.O.[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:19][C:13]1[CH:12]=[C:11]2[C:16]([CH2:17][CH2:18][N:9]([CH:7]([CH3:8])[CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 19067193HCID 19067193, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 19067154HCID 19067154, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.43 g of 2-[2-(ethoxycarbonyl)-1-methylethyl]-7-nitro-1,2,3,4-tetrahydroisoquinoline was dissolved in 10 ml of ethanol, and 1.23 g of tin chloride dihydrate was added to the solution. The solution was heated under reflux for 30 minutes to allow for the reaction to take place. The resulting solution was made basic by adding saturated aqueous solution of sodium bicarbonate, and the insoluble content was separated by using celite. The solution was extracted with ethyl acetate, washed with saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the residue was concentrated under reduced pressure to obtain 0.36 g of 7-amino-2-[2-(ethoxycarbonyl)-1-methylethyl]-1,2,3,4-tetrahydroisoquinoline, which was a brown oily product (yield: 93%).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 30 minutes
  3. customto allow for the reaction
  4. customthe insoluble content was separated
  5. extractionThe solution was extracted with ethyl acetate
  6. washwashed with saturated aqueous solution of sodium chloride
  7. dry with materialdried with anhydrous sodium sulfate
  8. customAfter separating the desiccant
  9. filtrationby filtration
  10. concentrationthe residue was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2b8b0855569242fd9e5e120643ab4259
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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