1,2-Cycloheptanedione → 2,4-Dichloro-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one

HRID 877464

Reaction equation

HRID 877464 reaction equation
[C:1]1(=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=O.Cl.[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[NH:19]N>CO.C(O)(C)=O.Cl>[Cl:18][C:16]1[CH:15]=[C:14]2[C:13](=[C:12]([Cl:11])[CH:17]=1)[NH:19][C:2]1[C:1](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2=1

Participants

5

Reactant 2

HCID 763651,2-CycloheptanedioneHCID 2723905(2,4-Dichlorophenyl)hydrazine monohydrochloride

Product 1

HCID 673655072,4-Dichloro-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-oneYield 9.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22641269Acetate-hydrochloric acidSolvent

Conditions

Temperature
60 °C

Procedure

Cycloheptane-1,2-dione (1 g, 7.9 mmol) was dissolved in MeOH (25 mL) and (2,4-dichlorophenyl)hydrazine hydrochloride (1.86 g, 8.7 mmol) in AcOH—HCl (3.5:1, 45 mL) was added and heated to 60° C. for 18 h. MeOH was removed in vacuo, the reaction mixture was basified with aqueous NaHCO3 (pH-8) and then extracted with EtOAc (3×25 mL), The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude product which was purified by silica gel chromatograph [EtOAc-hexane (9:1) as eluant] to give the title compound (0.2 g, 9.4%). 1H NMR (200 MHz, CDCl3, δ in ppm) 9.0 (br s, 1H), 7.54 (d, J=1.6 Hz, 1H), 7.33 (d, J=1.8 Hz, 1H), 3.11 (t, J=12.0 Hz, 2H), 2.90 (t, J=11.8 Hz, 2H), 2.13-2.20 (m, 4H).

Workup

  1. customMeOH was removed in vacuo
  2. extractionextracted with EtOAc (3×25 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product which
  6. customwas purified by silica gel chromatograph [EtOAc-hexane (9:1) as eluant]

Sources & evidence

ORD record
ord-c012c2257e6b467f97c4772296ca05b7
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Linked notes

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