HCID 15744974, compound → HCID 15744975, compound

HRID 327475Notes

Reaction equation

HRID 327475 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][CH2:10][CH:9]([N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[CH2:8]2>Br>[OH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][CH2:10][CH:9]([N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[CH2:8]2

Participants

3

Reactant 1

HCID 15744974HCID 15744974, compound

Product 1

HCID 15744975HCID 15744975, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 1,2,3,4-tetrahydro-8-methoxy-N,N-dipropyl-3-quinolinamine (0.98 g) in hydrobromic acid (20 mL of 48%) was heated at 155° C. for 6 hours. The solution was cooled, evaporated, and partitioned between ethyl acetate and saturated sodium bicarbonate solution. The aqueous phase was re-extracted with ethyl acetate and the combined organic phases were evaporated to give 0.88 g of 1,2,3,4-tetrahydro-8-hydroxy-N,N-dipropyl-3-quinolinamine as an oil.

Workup

  1. temperatureThe solution was cooled
  2. customevaporated
  3. custompartitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. extractionThe aqueous phase was re-extracted with ethyl acetate
  5. customthe combined organic phases were evaporated

Sources & evidence

ORD record
ord-80ac751ed94b436e95f8e7afb1bdba8f
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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