Pyridinium chloride → HCID 11466025, compound

HRID 859234Notes

Reaction equation

HRID 859234 reaction equation
C([O:3][C:4](=[O:36])[C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:13](=[O:35])[NH:14][C:15]3[C:20]([C:21]=2[C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=2[O:29]C)=[CH:19][C:18]([C:31]([F:34])([F:33])[F:32])=[CH:17][CH:16]=3)=[CH:7][CH:6]=1)C.Cl.N1C=CC=CC=1>>[Cl:28][C:26]1[CH:25]=[CH:24][C:23]([OH:29])=[C:22]([C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:31]([F:32])([F:33])[F:34])[CH:19]=3)[NH:14][C:13](=[O:35])[C:12]=2[S:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:36])=[O:3])=[CH:6][CH:7]=2)[CH:27]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 69666250HCID 69666250, compound

Product 1

HCID 11466025HCID 11466025, compoundYield 84%

Conditions

Temperature
220 °C

Procedure

A 25 mL round-bottomed flask equipped with a stir bar and a 19 cm glass sleeve was charged with 0.27 g (0.51 mmol) of 4-[4-(5-Chloro-2-methoxy-phenyl)-2-oxo-6-trifluoromethyl-1,2-dihydro-quinolin-3-ylsulfanyl]-benzoic acid ethyl ester and 2.7 g (23.3 mmol) of pyridine hydrochloride. The flask was flushed with nitrogen and a pipet emitting a stream of nitrogen was placed into the glass sleeve. The flask was placed in an oil bath pre-heated to 220° C. The TLC after 40 minutes showed the reaction was complete. The mixture was poured into 150 ml of 1 N HCl and then sonicated for 5 minutes to completely dissolve the pyridine hydrochloride. The white solid precipitate was filtered, washed with 1N HCl and dried to a constant weight to afford 0.21 g (84%) of the title compound. 1H NMR 300 MHz (DMSOd6) 6.98 (d, 1H, J=8.7 Hz), 7.25 (m, 4H), 7.35 (dd, 1H, J=6.1, 2.7 Hz), 7.59 (d, 1H, J=8.5, Hz), 7.75 (d, 2H, J=8.5 Hz), 7.91 (1H, dd, J=8.7, 1.8 Hz). IR cm−1 3206 (br), 1684, 1654, 1628, 1594, 1314. MS m/z 490 (M−H).

Workup

  1. customA 25 mL round-bottomed flask equipped with a stir bar
  2. customThe flask was flushed with nitrogen
  3. customThe flask was placed in an oil bath
  4. additionThe mixture was poured into 150 ml of 1 N HCl
  5. customsonicated for 5 minutes
  6. dissolutionto completely dissolve the pyridine hydrochloride
  7. filtrationThe white solid precipitate was filtered
  8. washwashed with 1N HCl
  9. customdried to a constant weight

Sources & evidence

ORD record
ord-89a37cf3d5ea45e1beb4ca2476c19b6b
Source dataset
uspto-grants-2006_12
Patent number
US07151180B2

Reaction notes

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