Ammonium Hydroxide → 1-Methyl-7-nitro-3,4-dihydroisoquinoline

HRID 369982Notes

Reaction equation

HRID 369982 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]=1.[N+:12]([O-])([O-:14])=[O:13].[K+].[OH-].[NH4+]>>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:5][CH2:4][N:3]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 2315021-Methyl-3,4-dihydroisoquinoline

Product 1

HCID 109322281-Methyl-7-nitro-3,4-dihydroisoquinoline

Procedure

1-Methyl-3,4-dihydroisoquinoline (4.25 g, 29.3 mmol) was dissolved in ice cold concentrated sulfuric acid (15 ml) and to this was added potassium nitrate (3.25 g, 32.2 mmol) portionwise with cooling. The mixture was stirred overnight, poured over ice, basified with concentrated ammonium hydroxide, and the precipitated solid was collected, washed with water and dried: 4.47 g (80%), MS (M+H)+ 191, 1H NMR (D2O), 8.30 (d, 1H), 8.22 (dd, 1H), 7.39 (d, 1H), 3.80-3.62 (m, 2H), 2.92-2.70 (m, 2H), 2.48 (broad s, 3H).

Workup

  1. temperaturewith cooling
  2. additionpoured over ice
  3. customthe precipitated solid was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5cffc12037354434a37b3a773f26cd97
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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