Nitric Acid → 5-Methoxy-1-methyl-4-nitroindole-2-carboxylic acid methyl ester

HRID 430930Notes

Reaction equation

HRID 430930 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]([C:9]1[N:10]([CH3:20])[C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=2)=[O:8]>CC(O)=O>[CH3:5][O:6][C:7]([C:9]1[N:10]([CH3:20])[C:11]2[C:16]([CH:17]=1)=[C:15]([N+:1]([O-:4])=[O:2])[C:14]([O:18][CH3:19])=[CH:13][CH:12]=2)=[O:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 4777906Methyl 5-methoxy-1-methyl-1H-indolecarboxylate

Product 1

HCID 206071685-Methoxy-1-methyl-4-nitroindole-2-carboxylic acid methyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of concentrated HNO3 (2 mL) in AcOH (9 mL) was added to a solution of 8 (830 mg, 3.79 mmol) in AcOH (54 mL) at 0° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 2 h. The reaction mixture was poured over ice, filtered and the precipitate washed with H2O. The precipitate was dissolved in CH2Cl2 and filtered through a short column of silica gel to afford 9 (780 mg, 78%) as a yellow solid; Rf=0.53 (50% EtOAc/hexanes); 1H NMR (CDCl3): δ 7.58 (1H, d), 7.55 (1H, s), 7.18 (1H, d), 4.11 (3H, s), 4.02 (3H, s), 3.94 (3H, s).

Workup

  1. additionthe addition
  2. additionThe reaction mixture was poured over ice
  3. filtrationfiltered
  4. washthe precipitate washed with H2O
  5. dissolutionThe precipitate was dissolved in CH2Cl2
  6. filtrationfiltered through a short column of silica gel

Sources & evidence

ORD record
ord-77930364b4224033b7049319aa437585
Source dataset
uspto-grants-2003_12
Patent number
US06656926B2

Reaction notes

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