Sodium Hydroxide → 6-Methyl-5-nitroisoquinoline

HRID 1042245Notes

Reaction equation

HRID 1042245 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[N+:12]([O-])([O-:14])=[O:13].[K+].[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 6409596-Methylisoquinoline

Product 1

HCID 250590506-Methyl-5-nitroisoquinolineYield 95%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

6-Methylisoquinoline (2.00 g, 14 mmol) was taken up in sulfuric acid (25.0 mL) and the mixture cooled down to 0° C. The reaction was treated with potassium nitrate (2.8 g, 28 mmol) which was added in portions. After addition was complete, the reaction was stirred for about 1.5 h at 0° C. The reaction was poured onto crushed ice and basified with 5N NaOH. The solid that precipitated was collected by suction filtration, washed with water and dried to give the product (2.5 g, 95%) as a tan solid. MS (ESI, pos. ion) m/z: 189.1 [M+H]+

Workup

  1. additionwas added in portions
  2. additionAfter addition
  3. additionThe reaction was poured
  4. customonto crushed ice
  5. customThe solid that precipitated
  6. filtrationwas collected by suction filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-a85f3b0f423f46a4aabb657656021ab8
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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