Nitric Acid → 1-methyl-5-nitroIsoquinoline

HRID 559480Notes

Reaction equation

HRID 559480 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 D8 (1 g, 7 mmol) in sulfuric acid (2.5 ml) was cooled (<4° C.) and concentrated nitric acid (1 ml) added over 10 min. Reaction was stirred for 30 min 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 using DCM. Organic phase was separated, dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound as a white solid.

Workup

  1. additionadded over 10 min
  2. customReaction
  3. temperatureAfter cooling the reaction mixture
  4. extractionfollowed by extraction
  5. customOrganic phase was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b162419f5889406aac10c6f821d65eda
Source dataset
uspto-grants-2011_11
Patent number
US08063078B2

Reaction notes

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