Ammonia → 8-Amino-3-methyl-5,6,7,8-tetrahydroquinoline dihydrochloride

HRID 2071597Notes

Reaction equation

HRID 2071597 reaction equation
[ClH:1].[Cl:2][CH:3]1[C:12]2[N:11]=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1.Cl.[NH3:15]>CO.CCOCC>[ClH:2].[ClH:1].[NH2:15][CH:3]1[C:12]2[N:11]=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 214117248-Chloro-3-methyl-5,6,7,8-tetrahydroquinoline hydrochloride

Product 1

HCID 123582218-Amino-3-methyl-5,6,7,8-tetrahydroquinoline dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The 8-chloro product of Example 2 (17 g.) was dissolved in methanol saturated with ammonia (400 ml.) and heated at 80° in a stainless steel bomb for 24 hours. The solvnet was removed in vacuo and the residual oil titurated with anhydrous ether (3 × 50 ml.) and the triturates discarded. The oily solid was dissolved in water the pH adjusted to 9.0 with sodium carbonate and extracted with ether (3 × 150 ml.). The combined extracts were dried (MgSO4) and the solvent removed in vacuo to give a pale yellow oil (5.5 g.). A sample (500 mg) was dissolved in anhydrous ether (25 ml.) and the solution treated with excess ethereal hydrogen chloride and the resultant solid recrystallised from methanol-ether to give 8-amino-3-methyl-5,6,7,8-tetrahydroquinoline dihydrochloride quarter hydrate as colourless needles m.p. 210° C.

Workup

  1. customThe solvnet was removed in vacuo
  2. dissolutionThe oily solid was dissolved in water the pH
  3. extractionextracted with ether (3 × 150 ml.)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give a pale yellow oil (5.5 g.)
  7. customthe resultant solid recrystallised from methanol-ether

Sources & evidence

ORD record
ord-141dbe8c2f094d3095aa4ed548e1c96d
Source dataset
uspto-grants-1977_09
Patent number
US04048175

Reaction notes

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