Phosphorus oxychloride → HCID 69670990, compound

HRID 1497578Notes

Reaction equation

HRID 1497578 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[CH:12][N:11]=2)=O)=[C:4]([O:26][CH3:27])[CH:3]=1.O=P(Cl)(Cl)Cl>>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]2[N:11]3[CH:12]=[C:13]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[CH:14]=[CH:15][C:10]3=[N:9][N:8]=2)=[C:4]([O:26][CH3:27])[CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67599708HCID 67599708, compound

Product 1

HCID 69670990HCID 69670990, compoundYield 75%

Conditions

Temperature
90 °C

Procedure

A flask was charged with the crude 4-chloro-2-methoxy-N′-(5-(4-methoxyphenyl)pyridin-2-yl)-benzohydrazide and POCl3 (13 mL), and the mixture was stirred at 80-100° C. overnight. The mixture was evaporated and the residue was adjusted to pH=9 with aqueous Na2CO3, then it was extracted with ethyl acetate (50 mL×4). The extract was dried over anhydrous Na2SO4 and the solvent was removed by evaporation. The crude product was purified by chromatography on silica (petroleum ether:ethyl acetate=1:1 to 0:1) to give the title compound as white solids (208 mg, 75.0% yield). 1H NMR (DMSO-d6): 8.17 (m, 1H), 7.92 (dd, J=9.6 and 1.2 Hz, 1H), 7.77 (dd, J=9.6 and 1.8 Hz, 1H), 7.68-7.62 (m, 3H), 7.40 (d, J=2.1 Hz, 1H), 7.25 (dd, J=8.1 and 2.1 Hz, 1H), 7.04 (d, J=6.6 Hz, 2H), 3.88 (s, 3H), 3.80 (s, 3H). MS: m/z 366.2 [M+H+].

Workup

  1. customThe mixture was evaporated
  2. extractionit was extracted with ethyl acetate (50 mL×4)
  3. dry with materialThe extract was dried over anhydrous Na2SO4
  4. customthe solvent was removed by evaporation
  5. customThe crude product was purified by chromatography on silica (petroleum ether:ethyl acetate=1:1 to 0:1)

Sources & evidence

ORD record
ord-75662ac8e0f24d87b4ca48a0a333a04a
Source dataset
uspto-grants-2015_12
Patent number
US09199983B2

Reaction notes

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