Hydrochloric Acid → HCID 44549393, compound

HRID 2238365Notes

Reaction equation

HRID 2238365 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[N:5](C(OC(C)(C)C)=O)[CH2:4]1.Cl>O1CCOCC1>[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

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 153804133-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indole

Product 1

HCID 44549393HCID 44549393, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of tert-butyl 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-3-carboxylate [J. Org. Chem., 1998, 63, 9414-9420] (101) (600 mg, 1.65 mmol) in dioxane (15 mL) was saturated with dry HCl, stirred at 20° C. for 1, and then evaporated under reduced pressure below 30° C. The residue was partitioned between CH2Cl2 and dilute aqueous KHCO3 and the organic phase was washed with water, dried, and then filtered rough a column of silica gel to give 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole (102) (372 mg, 86%) as a red solid: mp (CH2Cl2/petroleum ether) 100-101° C.; 1H NMR [(CD3)2SO] δ 8.11 (d, J—8.7 Hz, 1H), 7.87 (d, J=8.4 Hz, 1H), 7.65 (s, 1H), 7.55 (ddd, J=8.2, 7.0, 1.2 Hz, 1H), 7.40 (ddd, J=8.7, 6.8, 1.0 Hz, 1H), 6.27 (br s, 1H, 4.23-4.15 (m, 1H), 3.89 (dd, J=11.0, 3.7 Hz, 1H), 3.81 (t, J=9.7 Hz, 1H), 3.78-3.66 (m, 2H). Anal. (C13H11ClN2O2) C, H, N.

Workup

  1. customevaporated under reduced pressure below 30° C
  2. customThe residue was partitioned between CH2Cl2 and dilute aqueous KHCO3
  3. washthe organic phase was washed with water
  4. customdried
  5. filtrationfiltered rough a column of silica gel

Sources & evidence

ORD record
ord-508ce0b7c4fc4d43965cdd3dd14b3516
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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