Ammonium Hydroxide → HCID 21584357, compound

HRID 369988Notes

Reaction equation

HRID 369988 reaction equation
[CH2:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][N:5]=1)[CH2:2][CH3:3].[N+:14]([O-])([O-:16])=[O:15].[K+].[OH-].[NH4+]>S(=O)(=O)(O)O>[N+:14]([C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][N:5]=[C:4]2[CH2:1][CH2:2][CH3:3])=[CH:9][CH:10]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 13165142HCID 13165142, compound

Product 1

HCID 21584357HCID 21584357, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 1-propyl-3,4-dihydroisoquinoline (7.4 g, 42 mmol) [E. Spath, F. Berger, and W. Kuntara, Chem. Ber., 1930, 63B, 134] in concentrated sulfuric acid (100 ml) at 0° C. was added in a single portion potassium nitrate (4.5 g, 45 mmol). The solution was allowed to slowly warm to ambient temperature overnight. The reaction mixture was poured onto ice and was basified with concentrated ammonium hydroxide. The resulting solid that formed in the cooled solution could not be filtered off satisfactorily. Hence, the reaction mixture was extracted twice with dichloromethane and the dried (magnesium sulfate) organic phases were concentrated in vacuo to give the intermediate 7-nitro-1-propyl-3,4-dihydroisoquinoline as an oil (8.78 g, 94%). This solid was taken up in methanol (200 ml), cooled to 0° C., and sodium borohydride (3.0 g) was added in portions over 0.5 h. After stirring for an additional 0.5 h, the reaction mixture was acidified to pH 5 using 6M hydrochloric acid. The solvent was concentrated at the rotoevaporator and the residue was partitioned between dichloromethane and dilute sodium hydroxide solution. The dried (magnesium sulfate) organic phase was concentrated to give the crude product as the free base. This was taken up in ethanol (200 ml) and hydrochloric acid in ethanol was added until acidic. The resulting solid which formed was collected to afford the title compound (5.60 g, 52%) as a pale yellow solid, m.p. 229-30.5° C. (dec.).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. customThe resulting solid that formed in the cooled solution could not
  3. filtrationbe filtered off satisfactorily
  4. extractionHence, the reaction mixture was extracted twice with dichloromethane
  5. dry with materialthe dried (magnesium sulfate) organic phases
  6. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-2b185634b4a940bcaea0ad7680ac00c0
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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