Potassium Nitrate → HCID 44549537, compound

HRID 2238391Notes

Reaction equation

HRID 2238391 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=[CH:15][C:9]=3[CH:8]=[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[C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([N+:19]([O-:21])=[O:20])=[CH:7][C:6]=2[NH:5][CH2:4]1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 59303232HCID 59303232, compound

Product 1

HCID 44549537HCID 44549537, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of amine 136 (900 mg, 3.43 mmol) in conc. H2SO4 (9 mL) was cooled to −5° C. and treated with powdered KNO3 (520 mg, 5.14 mmol). The mixture was stirred at 0° C. for a further 15 min, then poured into ice-water and the solid was collected Chromatography on silica gel, eluting with petroleum ether/EtOAc (3:1), followed by two recrystallizations from CH2Cl2/iPr2O gave 1-(chloromethyl)-5,9-dinitro-1,2-dihydro-3H-benzo[e]indole (137) (394 mg, 37%) as a red solid: mp 130-131° C.; 1H [(CD3)2SO] δ 8.21 (dd, J=8.6, 1.1 Hz, 1H), 8.10 (dd, J=7.6, 1.1 Hz, 1 H), 7.75 (s, 1H), 7.44 (dd, J=−8.6, 7.6 Hz, 1H), 7.02 (s, 1H), 3.89-3.81 (m, 1H), 3.72-3.62 (m, 2H), 3.41-3.35 (m, 2H). Anal. (C13H10ClN3O4) C, H, N, Cl.

Workup

  1. customthe solid was collected Chromatography on silica gel
  2. washeluting with petroleum ether/EtOAc (3:1)
  3. customfollowed by two recrystallizations from CH2Cl2/iPr2O

Sources & evidence

ORD record
ord-11193095e11d4306844e25d618341cfe
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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