Sodium Hydroxide → (8S)-5,6,7,8-Tetrahydroquinolin-8-amine

HRID 2055816Notes

Reaction equation

HRID 2055816 reaction equation
Cl.[NH2:2][C@@H:3]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1.[OH-].[Na+]>O>[NH2:2][C@@H:3]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69295681(S)-8-amino-5,6,7,8-tetrahydroquinoline hydrochloride

Product 1

HCID 12031071(8S)-5,6,7,8-Tetrahydroquinolin-8-amineYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-8-amino-5,6,7,8-tetrahydroquinoline hydrochloride (23.4 kg, 106 mol) was dissolved in deionized water (60 L) and neutralized to pH 7 with a 50% sodium hydroxide solution (˜11.5 kg). The mixture was extracted with dichloromethane (126 kg). The pH of the aqueous layer was re-adjusted to 7 with 50% NaOH, and was extracted again with dichloromethane (126 kg). The dichloromethane fractions are then discarded. The pH of the aqueous layer was increased to 13 with 50% NaOH. The aqueous layer was then extracted with dichloromethane (2×126 kg). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo to afford (S)-8-amino-5,6,7,8-tetrahydroquinoline (12.7 kg, 81% yield, purity: 96% by HPLC) as a dark brown oil. 1H NMR (CDCl3) δ 1.64-1.84 (m, 2H), 1.94-2.01 (m, 1H), 2.14-2.23 (m, 1H), 2.69-2.87 (m, 2H), 3.99 (dd, 1H, J=7.7, 5.3 Hz), 7.06 (dd, 1H, J=7.7, 4.4 Hz), 7.36 (d, 1H, J=7.5 Hz), 8.41 (d, 1H, J=4.4 Hz).

Workup

  1. extractionThe mixture was extracted with dichloromethane (126 kg)
  2. extractionwas extracted again with dichloromethane (126 kg)
  3. temperatureThe pH of the aqueous layer was increased to 13 with 50% NaOH
  4. extractionThe aqueous layer was then extracted with dichloromethane (2×126 kg)
  5. dry with materialThe combined organic layers were dried (sodium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40896e85c5564aae86ee3c87e2079e15
Source dataset
uspto-grants-2008_02
Patent number
US07332605B2

Reaction notes

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