Hydrochloric Acid → HCID 58914687, compound

HRID 1297769Notes

Reaction equation

HRID 1297769 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([O:30]C)=[C:25]([CH3:32])[CH:24]=2)([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[C:6]1=[O:33].Cl.N1C=CC=CC=1.Cl>[Cu].C(OCC)(=O)C>[Cl:1][C:2]1[CH:37]=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:23]2[CH:24]=[C:25]([CH3:32])[C:26]([OH:30])=[C:27]([CH3:29])[CH:28]=2)([C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)[C:6]1=[O:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chloride2×HCID 58914732HCID 58914732, compound

Product 1

HCID 58914687HCID 58914687, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
190 °C

Procedure

Evaporate 1-(2-chloro-benzyl)-3-(4-methoxy-3,5-dimethyl-phenyl)-3-(4-nitro-phenyl)-1,3-dihydro-indol-2-one (62 mg, 0.12 mmol) into a vial and add pyridine hydrochloride (300-500 mg). Suspend the vial, by means of a copper wire, in an oil bath heated to 180-200° C. so that the entire vial, except the cap, is immersed in the bath. When the pyridine hydrochloride melts, stir to effect a homogeneous solution. Heat for 1.5 h and then allow to cool. Treat the resulting solid with 1N HCl solution and ethyl acetate until all solids are dissolved and transferred to a separatory funnel. Extract the aqueous portion with ethyl acetate (2×). Combine the organic portions and wash with brine, then dry (MgSO4), filter and concentrate in vacuo to give a yellow gum. Purify by flash chromatography (gradient of 10% EtOAc/hexanes to 33% EtOAc/hexanes) followed by trituration in diethyl ether and drying under house vacuum to obtain 24 mg (40%) of the title compound as a pale yellow solid. MS (ES): m/z=499 (M+1), 497 (M−1); 1H NMR(DMSO-d6): δ8.43 (s, 1H), 8.24 (d, J=9 Hz, 2H), 7.57-7.43 (m, 4H), 7.37-7.23 (m, 3H), 7.15 (t, J=8 Hz, 1H), 7.01 (m, 2H), 6.76 (s, 2H), 5.11 (s, 2H), 2.12 (s, 6H).

Workup

  1. temperatureHeat for 1.5 h
  2. temperatureto cool
  3. dissolutionare dissolved
  4. customtransferred to a separatory funnel
  5. extractionExtract the aqueous portion with ethyl acetate (2×)
  6. washCombine the organic portions and wash with brine
  7. dry with materialdry (MgSO4)
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customto give a yellow gum
  11. customPurify by flash chromatography (gradient of 10% EtOAc/hexanes to 33% EtOAc/hexanes)
  12. customdrying under house vacuum

Sources & evidence

ORD record
ord-262fbbdf4129411d83c1f5ab911cd947
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

Loading…