Nitric Acid → HCID 22627413, compound

HRID 278133Notes

Reaction equation

HRID 278133 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[C:6]1[CH2:18][CH2:19][CH3:20].[N+:25]([O-])([OH:27])=[O:26]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[C:7]([N+:25]([O-:27])=[O:26])=[C:6]1[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 22627144HCID 22627144, compound

Product 1

HCID 22627413HCID 22627413, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 1-(2-chlorobenzyl)-2-propylindole-6-carboxylate (200 mg) in trifluoroacetic acid (2 ml) was added concentrated nitric acid (0.3 ml) at 0° C. After stirred at 0° C. for 30 minutes, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel eluting with a mixture of ethyl acetate and hexane (1:3) to give methyl 1-(2-chlorobenzyl)-3-nitro-2-propylindole-6-carboxylate (73 mg) as pale yellow crystals.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with aqueous sodium bicarbonate, water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography on silica gel eluting with a mixture of ethyl acetate and hexane (1:3)

Sources & evidence

ORD record
ord-3e932f43f82044bd9ab5195a6ff43596
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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