O-Xylene → HCID 18918418, compound

HRID 1291828Notes

Reaction equation

HRID 1291828 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[C:11](=[O:20])[C:10]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C(C)=CC=CC=1.C(O)CC(C)C.Cl.Cl[C:43]1[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=1>C(N(CC)CC)C>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[C:11](=[O:20])[C:10]([N:21]2[CH2:22][CH2:23][N:24]([C:43]3[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=3)[CH2:25][CH2:26]2)=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 31260Isoamyl AlcoholHCID 818524-Chloropyridine hydrochloride2×HCID 18918333HCID 18918333, compound

Product 1

HCID 18918418HCID 18918418, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

A mixture of the product of step (v) (1.1 g), xylene (110 ml), isoamyl alcohol (11 ml), 4-chloropyridine hydrochloride (1.1 g) and triethylamine (11 ml) was heated to reflux and stirred for 30 hours. During this period extra aliquots of 4-chloropyridine hydrochloride (6×1.1 g) and triethylamine (3×11 ml) were added at intervals. The reaction mixture was evaporated to dryness and the residue was purified by flash chromatography on silica by elution with methanol/dichloromethane/concentrated ammonia (20:200:1) to give 1-benzyl-3-(4-(4-pyridyl)piperazin-1-yl)-7-methoxy-4-quinolone (780 mg) as an orange-red solid: NMR (d6DMSO) δ 3.2 (4H, m), 3.75 (3H, s), 3.80 (4H, m), 5.55 (2H, s), 6.90 (2H, m), 7.30 (7H, m), 7.88 (1H, s), 8.13 (1H, d), 8.24 (2H, d); m/Z 427 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customThe reaction mixture was evaporated to dryness
  4. customthe residue was purified by flash chromatography on silica by elution with methanol/dichloromethane/concentrated ammonia (20:200:1)

Sources & evidence

ORD record
ord-347d1f626bf647adb10bfc189262035d
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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