Sulfuric Acid → 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7 carboxamide

HRID 2238397Notes

Reaction equation

HRID 2238397 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][C:9]=3[C:8]([N+:18]([O-:20])=[O:19])=[CH:7][C:6]=2[NH:5][CH2:4]1.[OH:21]S(O)(=O)=O>O>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][C:14]([C:16]([NH2:17])=[O:21])=[CH:15][C:9]=3[C:8]([N+:18]([O-:20])=[O:19])=[CH:7][C:6]=2[NH:5][CH2:4]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 445494011-(chloromethyl)-7-cyano-5-nitro-1,2-dihydro-3H-benzo[e]indole

Product 1

HCID 445493911-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7 carboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 144 (100 mg, 0.35 mmol) in a mixture of cone. H2SO4 (1.8 mL) and water (0.2 mL) was heated at 65° C. for 1 h, then cooled and neutralized with saturated aqueous KHCO3. The precipitate was collected, washed with water, and dissolved in warm EtOAc. The solution was filtered through a column on silica gel and then concentrated and diluted with iPr2O to give 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7 carboxamide (145) (92 mg, 86%) as a red solid: mp (EtOAc/iPr2O)>300° C.; 1H NMR [(CD3)2SO] δ 8.61 (d, J=1.3 Hz, 1H), 8.09, 7.39 (2 br s, 2H), 7.95 (dd, J=8.8, 1.7 Hz, 1H), 7.89 (d, J=8.7 Hz, 1H), 7.66 (s, 1H), 6.54 (s, 1H), 426-4.18 (m, 1H), 3.91 (dd, J=11.0, 3.8 Hz, 1H), 3.86 (td, J=9.9, 2.3 Hz, 1H), 3.78 (dd, J=11.0, 8.5 Hz, 1H), 3.72 (dd, J=10.3, 2.6 Hz, 1H). Anal. (C14H12ClN3O3) C, H, N.

Workup

  1. temperaturecooled
  2. customThe precipitate was collected
  3. washwashed with water
  4. dissolutiondissolved in warm EtOAc
  5. filtrationThe solution was filtered through a column on silica gel
  6. concentrationconcentrated
  7. additiondiluted with iPr2O

Sources & evidence

ORD record
ord-86cff235b419493dbb311ff1476fa8e2
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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