Nitric Acid → 1-methyl-5-nitroIsoquinoline

HRID 494206Notes

Reaction equation

HRID 494206 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[N+:12]([O-])([OH:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 11430Potassium CarbonateHCID 155921-Methylisoquinoline

Product 1

HCID 126479501-methyl-5-nitroIsoquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

A solution 1-methylisoquinoline (D91) (1 g, 7 mmol) in sulfuric acid (2.5 ml) was cooled (<4° C.) and concentrated nitric acid (1 ml) was added over 10 mins. The reaction was stirred for 30 mins and then heated at 60° C. for 2 h. After cooling, the reaction mixture was poured into ice water slurry (100 ml) and basified using solid potassium carbonate followed by extraction with DCM. The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo to afford the product as a white solid (1.05 g). 1H NMR (400 MHz, DMSO) δ (ppm): 8.69 (d, 1H), 8.59 (m, 2H), 8.11 (d, 1H), 7.88 (t, 1H), 2.99 (s, 3H).

Workup

  1. additionwas added over 10 mins
  2. temperatureAfter cooling
  3. extractionfollowed by extraction with DCM
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85977a9645644a19b7613e5e862ac353
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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