Ammonia → 1,2,3,4-Tetrahydro-7-nitroisoquinoline

HRID 1808331Notes

Reaction equation

HRID 1808331 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.S(=O)(=O)(O)O.[N+:16]([O-])([O-:18])=[O:17].[K+].N.Cl>>[N+:16]([C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][NH:2][CH2:1]2)=[CH:6][CH:7]=1)([O-:18])=[O:17]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 70461,2,3,4-TetrahydroisoquinolineHCID 24434Potassium Nitrate

Product 1

HCID 64248331,2,3,4-Tetrahydro-7-nitroisoquinolineYield 52.3%

Conditions

Temperature
0 °C

Procedure

1,2,3,4-Tetrahydroisoquinoline (50 g; 1 equiv.) was added at 0° C., in the course of 90 minutes, to 185 ml of sulfuric acid, and the reaction mixture was stirred for 30 minutes at 0° C. Potassium nitrate (40.7 g; 1.2 equiv.) was then added in portions, and stirring was carried out for 15 hours at room temperature. When the conversion was complete, the reaction mixture was shaken on 500 g of ice and adjusted to pH 8-9 with ammonia solution. Extraction with chloroform was then carried out 3 times, and the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The residue was taken up in IPA (500 ml) and cooled to 0° C., and hydrochloric acid (2 equiv.) was added. The resulting solid was filtered out and recrystallised from methanol. 7-Nitro-1,2,3,4-tetrahydroisoquinoline (35 g; 52.3%) was obtained in the form of a white solid.

Workup

  1. stirringstirring
  2. waitwas carried out for 15 hours at room temperature
  3. extractionExtraction with chloroform
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. temperaturecooled to 0° C.
  7. filtrationThe resulting solid was filtered out
  8. customrecrystallised from methanol

Sources & evidence

ORD record
ord-6fec767c26de44b59ad830e0f8a18859
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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