Ammonium Hydroxide → HCID 20196477, compound

HRID 652731Notes

Reaction equation

HRID 652731 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[CH3:6][CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9][CH2:8]1.[OH-].[NH4+]>S(=O)(=O)(O)O>[CH3:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([N+:1]([O-:4])=[O:2])=[CH:14][CH:15]=2)[CH:10]=[N:9][CH2:8]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 131435574-Methyl-3,4-dihydroisoquinoline

Product 1

HCID 20196477HCID 20196477, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a stirred solution of potassium nitrate (10 g) in conc-sulfuric acid (50 ml) was added slowly a solution of 3,4-dihydro-4-methylisoquinoline (12 g) in conc-sulfuric acid (50 ml) at -20°~-10° C. over a period of an hour. The reaction mixture was allowed to stir at ambient temperature for 3 hours and heated at 60° C. for 1.5 hours. The reaction mixture was poured onto ice, and adjusted to alkaline pH with 28% ammonium hydroxide under cooling. The resulting brown solid was filtered off, washed with water, and dried in vacuo to give 3,4-dihydro-4-methyl-7-nitroisoquinoline (14.63 g).

Workup

  1. temperatureheated at 60° C. for 1.5 hours
  2. additionThe reaction mixture was poured onto ice
  3. temperatureunder cooling
  4. filtrationThe resulting brown solid was filtered off
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-0eaaa7b491b24afa8d36f76a800c8025
Source dataset
uspto-grants-1987_06
Patent number
US04673676

Reaction notes

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