Hydrochloric Acid → HCID 71542043, compound

HRID 1023177Notes

Reaction equation

HRID 1023177 reaction equation
[OH:1]/[N:2]=[C:3](/[NH2:17])\[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2.[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C:27]#N)[CH:22]=[CH:23][C:24]=1[Cl:25].C(O)C.Cl>C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C:27]2[O:1][N:2]=[C:3]([CH2:4][O:5][C:6]3[CH:7]=[C:8]4[C:13](=[CH:14][CH:15]=3)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]4)[N:17]=2)[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6042543,4-DichlorophenylcyanamideHCID 28203387HCID 28203387, compound

Product 1

HCID 71542043HCID 71542043, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-N′-hydroxy-2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetimidamide (0.1 g, 0.425 mmol) in ethyl acetate (10 mL) was added a 0.5M solution of zinc chloride (0.073 mL, 0.510 mmol) followed by N-(3,4-dichlorophenyl)cyanamide (0.080 g, 0.425 mmol) and stirred at room temperature for 12 h. Then reaction mixture was concentrated. Ethanol (10.00 mL) was added along with HCl (0.1 mL, 3.29 mmol) and the reaction mixture was heated at 80° C. for 6 h. The reaction mixture was concentrated and basified with sodium bicarbonate solution, then the resulting solid was filtered and was washed with acetonitrile to give 6-((5-((3,4-dichlorophenyl)amino)-1,2,4-oxadiazol-3-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one as a white solid (12 mg, 6.8% yield). 1H NMR 400 MHz, DMSO-d6: δ 2.41 (t, J=15.20 Hz, 2H), 2.84 (t, J=15.20 Hz, 2H), 4.94 (s, 2H), 6.77-6.79 (m, 1H), 6.84-6.87 (m, 1H), 6.93 (d, J=2.80 Hz, 1H), 7.30 (s, 1H), 7.37 (s, 1H), 7.80 (s, 1H), 9.91 (s, 1H). LCMS: RT 1.963 min; LCMS (ES-API), m/z 403.0 [M−H]−.

Workup

  1. customThen reaction mixture
  2. concentrationwas concentrated
  3. temperaturethe reaction mixture was heated at 80° C. for 6 h
  4. concentrationThe reaction mixture was concentrated
  5. filtrationthe resulting solid was filtered
  6. washwas washed with acetonitrile

Sources & evidence

ORD record
ord-5bc00b0c8f164dbdb39a6546eb9e35f9
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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