Hydrochloric Acid → 6-chloro-7-ethoxy-8-nitro-9H-beta-carboline

HRID 552178Notes

Reaction equation

HRID 552178 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Cl:5][C:6]1[CH:7]=[C:8]2[C:16](=[C:17]([N+:20]([O-:22])=[O:21])[C:18]=1F)[NH:15][C:14]1[CH:13]=[N:12][CH:11]=[CH:10][C:9]2=1.Cl>CS(C)=O.O>[Cl:5][C:6]1[CH:7]=[C:8]2[C:16](=[C:17]([N+:20]([O-:22])=[O:21])[C:18]=1[O:1][CH2:2][CH3:3])[NH:15][C:14]1[CH:13]=[N:12][CH:11]=[CH:10][C:9]2=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 593375336-chloro-7-fluoro-8-nitro-9H-pyrido[3,4-b]indole

Product 1

HCID 671651336-chloro-7-ethoxy-8-nitro-9H-beta-carbolineYield 40%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Sodium ethoxide (232 mg, 3.4 mmol) was added to a solution of 6-chloro-7-fluoro-8-nitro-9H-β-carboline (200 mg, 0.76 mmol) in DMSO (4 ml) and the reaction mixture allowed to stir overnight. The reaction mixture was diluted with water and the pH of the solution was adjusted to about 4 by adding 1N HCl. The aqueous solution was extracted (3×) with EtOAc. The combined EtOAc layers were dried and evaporated. The crude product was purified by flash chromatography to give the desired product in 40-60% yield. 1H-NMR (300 MHz, DMSO-d6): δ 1.44 (t, 3H), 4.24 (q, 2H), 8.21 (d, 1H), 8.46 (d, 1H), 8.91 (s, 1H), 9.02 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 2.37 min. MS (M+H+): 291.9.

Workup

  1. extractionThe aqueous solution was extracted (3×) with EtOAc
  2. dry with materialThe combined EtOAc layers were dried
  3. customevaporated
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-3c8a1caabfde41629138a1baf00c92ac
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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