Hydrochloric Acid → HCID 178516420, compound

HRID 859985Notes

Reaction equation

HRID 859985 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](Cl)([OH:12])[C:6](O)=[C:5]2Cl.[Cl:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[Cl:24])[NH2:20].Cl.O1CCOCC1>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([OH:12])[CH:6]=[C:5]2[NH:20][C:19]1[CH:21]=[CH:22][C:23]([Cl:24])=[C:17]([Cl:16])[CH:18]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 72573,4-DichloroanilineHCID 312751,4-DioxaneHCID 69659655HCID 69659655, compound

Product 1

HCID 178516420HCID 178516420, compoundYield 47.4%

Procedure

Prepared using general procedure 1; 6-Fluoro-2,4-dichloroquinolinediol (2.5 g, 13.95 mmol), 3,4-dichloroaniline (4.5 g, 27.91 mmol), 5 mL of 4 M HCl in dioxane (20 mmol) were irradiated to 180° C. (400 W max) for 40 min. Pouring onto methanol followed by collection of the solids, afforded 2.136 g of material (6.61 mmol, 47%). 1H NMR (300 MHz, DMSO): 11.48(s, 2H), 8.74(s, 1H), 7.92(dd, 1H, J=10.70, 2.60 Hz), 7.65(d, 1H, J=8.88 Hz), 7.56(d, 1H, J=2.42 Hz), 7.49(d, 1H), 7.33(m, 2H), 5.89(s, 1H).

Workup

  1. customPrepared
  2. additionPouring onto methanol
  3. customfollowed by collection of the solids

Sources & evidence

ORD record
ord-437804517df54d27a0cdd996ee0426b6
Source dataset
uspto-grants-2006_12
Patent number
US07153865B2

Reaction notes

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