Hydrochloric Acid → 4-(5-nitro-1H-indol-3-yl)cyclohex-3-en-1-one

HRID 552938Notes

Reaction equation

HRID 552938 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]1[CH2:22][CH2:21][C:16]2(OCC[O:17]2)[CH2:15][CH:14]=1)([O-:3])=[O:2].Cl>CC(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]1[CH2:22][CH2:21][C:16](=[O:17])[CH2:15][CH:14]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 573848065-Nitro-3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1H-indole

Product 1

HCID 573845384-(5-nitro-1H-indol-3-yl)cyclohex-3-en-1-oneYield 88.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of compound 78 (0.1 g, 0.332 mmol) in acetone (5 mL) was treated with 10% aq. HCl (5 mL) at room temperature and stirred for 6 h. Acetone was evaporated and crude was basified using NH4OH solution (20 mL). The product was extracted into CH2Cl2 (2×20 mL), washed with brine (10 mL) and dried (Na2SO4). The CH2Cl2 layer was evaporated to obtain compound 79 (0.075 g, 88%) as a solid. mp 210-212° C.; 1H NMR (DMSO-d6) δ 2.59 (t, 2H, J=6.9 Hz), 2.90 (t, 2H, J=6.6 Hz), 3.11-3.12 (m, 2H), 6.24 (t, 1H, J=3.6 Hz), 7.57 (d, 1H, J=9.0 Hz), 7.76 (d, 1H, J=2.1 Hz), 8.03 (dd, 1H, J=2.1, 9.0 Hz), 8.71 (d, 1H, J=2.1 Hz), 11.95 (s, 1H); ESI-MS m/z (%): 257 (M+, 100).

Workup

  1. customAcetone was evaporated
  2. extractionThe product was extracted into CH2Cl2 (2×20 mL)
  3. washwashed with brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe CH2Cl2 layer was evaporated

Sources & evidence

ORD record
ord-6eeb0e6aa85140b49365f0527dc0a771
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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