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

HRID 583283

Reaction equation

HRID 583283 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-1d0ff4b61cd7498081d94b98fa6c49ec
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Linked notes

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