Sulfuric Acid → HCID 68692459, compound

HRID 2238418Notes

Reaction equation

HRID 2238418 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[C:13]([C:16]([O:18]C)=[O:17])[CH:14]=[CH:15][C:9]=3[C:8]([N+:20]([O-:22])=[O:21])=[CH:7][C:6]=2[N:5](C(=O)C(F)(F)F)[CH2:4]1.OS(O)(=O)=O>O>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=[CH:15][C:9]=3[C:8]([N+:20]([O-:22])=[O:21])=[CH:7][C:6]=2[NH:5][CH2:4]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 44549272HCID 44549272, compound

Product 1

HCID 68692459HCID 68692459, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

A suspension of 184 (314 mg, 0.75 mmol) in a mixture of conc. H2SO4 (4.5 mL) and water (0.5 mL) was stirred at 90° C. for 3 h, then cooled and diluted with water (80 mL). The solution was clarified by filtration and adjusted to pH 4 with aqueous NH3. The resulting precipitate was collected, dissolved in EtOAc and the solution was then filtered, concentrated under reduced pressure to a small volume and diluted with hexane to give 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-8-carboxylic acid (187) (226 mg, 95%) as a red solid: mp 205-208° C.; 1H NMR [(CD3)2SO] δ 13.3 (v br, 1H), 8.38 (d, J=1.3 Hz, 1H), 8.19 (d, J=9.1 Hz, 1H), 7.82 (dd, J=9.1, 1.6 Hz, 1H), 7.76 (s, 1H), 6.45 (s, 1H), 4.35-4.25 (m, 1H), 3.91-3.80 (m, 2H), 3.76 (dd, J=11.2, 8.5 Hz, 1H), 3.72 (dd, J=10.3, 2.8 Hz, 1H). Anal. C14H11ClN2O4) C, H, N.

Workup

  1. temperaturecooled
  2. filtrationThe solution was clarified by filtration
  3. customThe resulting precipitate was collected
  4. dissolutiondissolved in EtOAc
  5. filtrationthe solution was then filtered
  6. concentrationconcentrated under reduced pressure to a small volume
  7. additiondiluted with hexane

Sources & evidence

ORD record
ord-4f90247df6b64ea9a7aa6d466c6ce62f
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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