Sodium Bicarbonate → rac-5-{[2-(5-Fluoro-2-hydroxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylic acid

HRID 875328Notes

Reaction equation

HRID 875328 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:23]C)=[C:6]([CH2:8][CH2:9][NH:10][CH:11]2[CH2:20][CH2:19][CH2:18][C:17]3[N:16]=[C:15](C#N)[CH:14]=[CH:13][C:12]2=3)[CH:7]=1.[C:25](=[O:28])(O)[O-:26].[Na+]>Br.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:23])=[C:6]([CH2:8][CH2:9][NH:10][CH:11]2[CH2:20][CH2:19][CH2:18][C:17]3[N:16]=[C:15]([C:25]([OH:26])=[O:28])[CH:14]=[CH:13][C:12]2=3)[CH:7]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 89940804rac-5-{[2-(5-Fluoro-2-methoxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carbonitrile

Product 1

HCID 89940808rac-5-{[2-(5-Fluoro-2-hydroxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

72.8 g (223.73 mmol) of rac-5-{[2-(5-fluoro-2-methoxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carbonitrile were taken up in 360 ml of hydrobromic acid (48% in water) and initially stirred at boiling point for 12 h, then cooled to room temperature and allowed to stand at this temperature overnight. The reaction solution was then diluted with 400 ml of water and adjusted to pH 6 using saturated sodium bicarbonate solution. The crystals formed were filtered off with suction, washed with water and dried under reduced pressure at 50° C. This gave 59 g (178.59 mmol, 80% of theory) of the target compound.

Workup

  1. customfor 12 h
  2. customto stand at this temperature overnight
  3. customThe crystals formed
  4. filtrationwere filtered off with suction
  5. washwashed with water
  6. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-84345edf12d04a32a106081dbec76061
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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