Dimethyl Sulfoxide → 4-[1-(2-{[9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-yl]carbonyl}hydrazono)-ethyl]benzoic acid

HRID 992571Notes

Reaction equation

HRID 992571 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([C:18]([NH:20][NH2:21])=[O:19])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.[C:27]([C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=1)(=O)[CH3:28].CS(C)=O>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([C:18]([NH:20][N:21]=[C:27]([C:30]3[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=3)[CH3:28])=[O:19])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 114704-Acetylbenzoic AcidHCID 98214779-(2,5-Dichlorobenzyl)-9H-beta-carboline-3-carbohydrazide

Product 1

HCID 725951734-[1-(2-{[9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-yl]carbonyl}hydrazono)-ethyl]benzoic acidYield 73%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9-(2,5-dichlorobenzyl)-9H-β-carboline-3-carbohydrazide (100 mg, 0.25 mmole), 4-acetyl benzoic acid (50 mg, 0.3 mmole), DMSO (5 mL), and one drop of glacial acetic acid was stirred at room temperature for 12 hours. Ethyl acetate (50 ml) was added to the flask. The mixture was extracted with water and brine. The product crystallized from the organic phase was filtered, affording 97 mg (73%) of the title compound. 1H NMR (DMSO-d6) δ9.0 (s, 2H), 8.5 (d, 1H), 8.25 (s, 1H), 8.0-7.9 (m, 4H), 7.6-7.5 (m, 3H), 7.4-7.3 (m, 2H), 6.6 (s, 1H), 5.9 (s, 2H), 2.4 (s, 3H),MS (APCI; (M+H)+) m/z 531.

Workup

  1. extractionThe mixture was extracted with water and brine
  2. customThe product crystallized from the organic phase
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-b40b93e2322c4c9c9a7191f724779f64
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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