Water → HCID 57471240, compound

HRID 1044509Notes

Reaction equation

HRID 1044509 reaction equation
Cl.[NH2:2][CH:3]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16](Cl)[CH:15]=2)[C:11]2[CH:10]=[C:9]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4]1.O.NN.O.C(Cl)Cl>C(O)C.[Pd]>[ClH:20].[NH2:2][CH:3]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[CH:10]=[C:9]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 57471178HCID 57471178, compound

Product 1

HCID 57471240HCID 57471240, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(2-(7-Amino-8-(3,4-dichlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yloxy)ethyl)methanesulfonamide hydrochloride (50.0 mg, 0.104 mmol), Pd—C 10% (1.10 mg), and hydrazine monohydrate (522 mg, 10.4 mmol) were suspended in ethanol (5 ml) and stirred for 4 h under reflux. Water and CH2Cl2 were added, the mixture filtered, and the filtrate was extracted with CH2Cl2. The combined organic layers were washed with water, saturated NaCl solution, dried over Na2SO4, and concentrated to afford a residue that was purified by precipitation from diisopropylether. The residue was transferred to an HCl salt and finally gave the product as a white solid (31 mg, 72%).

Workup

  1. temperatureunder reflux
  2. filtrationthe mixture filtered
  3. extractionthe filtrate was extracted with CH2Cl2
  4. washThe combined organic layers were washed with water, saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford a residue that
  8. customwas purified by precipitation from diisopropylether

Sources & evidence

ORD record
ord-bdbc0317f30842c2b081cc3b7ae3b15d
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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