Potassium Nitrate → HCID 44549394, compound

HRID 2238366Notes

Reaction equation

HRID 2238366 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([N+:16]([O-:18])=[O:17])=[CH:7][C:6]=2[NH:5][CH2:4]1.[N+:19]([O-])([O-:21])=[O:20].[K+]>OS(O)(=O)=O>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[C:9]=3[C:8]([N+:16]([O-:18])=[O:17])=[CH:7][C:6]=2[NH:5][CH2:4]1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 44549393HCID 44549393, compound

Product 1

HCID 44549394HCID 44549394, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 102 (500 mg, 1.90 mmol) in conc. H2SO4 (5 mL) was cooled to −5° C. and treated with powdered KNO3 (288 mg, 2.85 mmol). The mixture was stirred at 0° C. for a further 15, in, then poured into ice-water and the solid was collected and dissolved in CH2Cl2. The solution was filtered through a column of silica gel and the product was recrystallised from EtOAc/iPr2O to give 1-(chloromethyl)-5,6-dinitro-1,2-dihydro-3H-benzo[e]indole (103) (446 mg, 76%) as a red solid: mp 206-207° C.; 1H NMR [(CD3)2SO] δ 8.23 (dd, J=8.7, 1.0 Hz, 1H), 8.00 (dd, J=7.7, 0.9 Hz, 1H), 7.76 (s, 1H), 7.67 (dd, J=8.4, 7.6 Hz, 1H), 6.72 (s, 1H), 4.32-4.22 (m, 1H), 3.94-3.83 (m, 2H), 3.83-3.75 (m, 2). Anal. (C13H10ClN3O4) C, H, N.

Workup

  1. customthe solid was collected
  2. dissolutiondissolved in CH2Cl2
  3. filtrationThe solution was filtered through a column of silica gel
  4. customthe product was recrystallised from EtOAc/iPr2O

Sources & evidence

ORD record
ord-6908e74f6aa54cfe988a9726297c1abf
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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