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

HRID 552952Notes

Reaction equation

HRID 552952 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 99.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of compound 78 (4.7 g, 15.650 mmol) in acetone (50 mL) was treated with 10% aq. HCl (50 mL) at room temperature and stirred for over night (14 h). Acetone was evaporated and crude was basified using 10% aq. NH4OH solution (100 mL). The precipitate was filtered off, washed with 10% NH4OH solution (2 10 mL) and water (2 10 mL). The product was dried under vacuum to obtain compound 79 (4.0 g, quantitative) as a solid. For spectral data, please see Example 23.

Workup

  1. customAcetone was evaporated
  2. filtrationThe precipitate was filtered off
  3. washwashed with 10% NH4OH solution (2 10 mL) and water (2 10 mL)
  4. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-538a0fbcbd674e3593977a24dd4f8866
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

Loading…