Ammonium Chloride → HCID 69671353, compound

HRID 1497571Notes

Reaction equation

HRID 1497571 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[O:24][CH3:25])=[N:16][N:17]=3)[CH:14]=2)=[CH:5][C:4]=1[N+:26]([O-])=O.[NH4+].[Cl-:30]>C(O)C.O.Cl.C(OCC)(=O)C.[Fe]>[ClH:30].[NH2:26][C:4]1[CH:5]=[C:6]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[O:24][CH3:25])=[N:16][N:17]=3)[CH:14]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 69671083HCID 69671083, compound

Product 1

HCID 69671353HCID 69671353, compoundYield 17.7%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 21866389Hydrogen chloride-ethyl acetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6-(4-methoxy-3-nitrophenyl)-3-(2-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine (80 mg, 0.21 mmol), iron (59 mg, 1.06 mmol) and NH4Cl (6 mg, 0.11 mmol) in ethanol (10 mL) and water (10 ml) was stirred for 3 h at 70° C. The mixture was concentrated under reduced pressure at 50° C. to remove ethanol, and was extracted with ethyl acetate (40 mL×4). The combined organic phase were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to give a product. The product was dissolved in HCl/ethyl acetate (2M, 20 mL), stirred at room temperature for 30 min, and concentrated to dryness to give the title compound (7.45 mg, 10.2% yield) as yellow solids. 1H NMR (DMSO-d6): 8.14 (m, 1H), 8.05 (dd, J=9.6 and 0.9 Hz, 1H), 7.88 (dd, J=9.6 and 1.5 Hz, 1H), 7.71-7.58 (m, 4H), 7.35 (d, J=8.1 Hz, 1H), 7.26-7.19 (m, 2H), 3.92 (s, 3H), 3.89 (s, 3H). MS: m/z 347.2 [M+H+].

Workup

  1. concentrationThe mixture was concentrated under reduced pressure at 50° C.
  2. customto remove ethanol
  3. extractionwas extracted with ethyl acetate (40 mL×4)
  4. dry with materialThe combined organic phase were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto give a product
  8. stirringstirred at room temperature for 30 min
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-08b0cf30219f4cce8e13ea7768e875d9
Source dataset
uspto-grants-2015_12
Patent number
US09199983B2

Reaction notes

Loading…