Sodium Bicarbonate → 5,6,7,8-Tetrahydro-5-[[2-(2-hydroxyphenyl)ethyl]amino]-2-quinolinecarboxylic acid

HRID 875307Notes

Reaction equation

HRID 875307 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][NH:11][CH:12]1[CH2:21][CH2:20][CH2:19][C:18]2[N:17]=[C:16](C#N)[CH:15]=[CH:14][C:13]1=2.[C:24](=[O:27])(O)[O-:25].[Na+]>Br.O>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][NH:11][CH:12]1[CH2:21][CH2:20][CH2:19][C:18]2[N:17]=[C:16]([C:24]([OH:25])=[O:27])[CH:15]=[CH:14][C:13]1=2

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 899408535,6,7,8-Tetrahydro-5-[[2-(2-methoxyphenyl)ethyl]amino]-2-quinolinecarbonitrile

Product 1

HCID 899407575,6,7,8-Tetrahydro-5-[[2-(2-hydroxyphenyl)ethyl]amino]-2-quinolinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

14.6 g (47.5 mmol) of 5-{[2-(2-methoxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carbonitrile were taken up in 100 ml of hydrobromic acid (48% in water) and stirred at boiling point for 5 hours. The reaction solution was then cooled to room temperature, diluted with water and adjusted to pH 6 with saturated sodium bicarbonate solution. The crystals formed were filtered off with suction, washed with water and air-dried. This gave 14.6 g (46.76 mmol, 98% of theory) of the target compound.

Workup

  1. customfor 5 hours
  2. customThe crystals formed
  3. filtrationwere filtered off with suction
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-48436bf087a84d2b8d5379688bc04ce1
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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