Ammonia → 2-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 1957514Notes

Reaction equation

HRID 1957514 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].N.[CH:15](O)=O>C=O>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]([CH3:15])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 284Formic AcidHCID 122162777-Nitroisoquinoline

Product 1

HCID 221158282-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

A solution of 4.00 g (18.7 mmol) of 7-nitroisoquinoline in 10 ml of formic acid and 17 ml of 38% aqueous formaldehyde was heated at reflux for 1 h. The reaction mixture was cooled, poured onto ice and basified with aqueous ammonia. The gummy residue which precipitated was extracted twice with methylene chloride. The dried (magnesium sulfate) organic phase was concentrated to give crude 7-nitro-2-methyl-1,2,3,4-tetrahydroisoquinoline as a thick oil. This oil was immediately taken up in ethanol (50 ml) and a solution of hydrochloric acid in ethanol was added until the solution was distinctly acidic to litmus. Ether was added to induce precipitation and the resulting solid was collected to give 3.99 g (93%) of the title compound as a yellow solid, m.p. 236°-8° C. (dec).

Workup

  1. temperatureat reflux for 1 h
  2. temperatureThe reaction mixture was cooled
  3. customThe gummy residue which precipitated
  4. extractionwas extracted twice with methylene chloride
  5. dry with materialThe dried (magnesium sulfate) organic phase
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-c64a81619cb54a33a60a9346af5bfd3e
Source dataset
uspto-grants-1998_07
Patent number
US05786364

Reaction notes

Loading…