Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Hydrazine hydrate (1:1) | HCID 24654 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66625463 | HCID 66625463 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58032165 | HCID 58032165 | — |
Reaction Steps
[Step 4] 102 mg of 1-acetyl-4-[(4-morpholinophenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid, 125 mg of WSCD.HCl, and 72 mg of HOBt.H2O were dissolved in 1 mL of dichloromethane, and 0.12 mL of hydrazine monohydrate was added to the solution. The mixture was stirred overnight at room temperature. After completion of the reaction, a saturated aqueous solution of sodium hydrogen carbonate was added to the mixture, and the mixture was extracted three times with chloroform. The extraction product was washed with saturated brine, dehydrated over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (methanol:chloroform=1:10), and thus 83 mg (cis:trans=3:1, 79) of the title compound was obtained as a brown oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09045423B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-c929fce561de4ffea4fc484d75f390b3 |
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| Source note | uspto-grants-2015_06 |
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