Pyridine → 3-Amino-4-(5-chloro-2-methoxyphenyl)-6-(trifluoromethyl)quinolin-2(1H)-one

HRID 1740869Notes

Reaction equation

HRID 1740869 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]([C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=2[NH:20][C:21](=[O:24])[CH2:22]Cl)=O)[CH:7]=1.[N:27]1C=CC=CC=1>C1C=CC=CC=1>[NH2:27][C:22]1[C:21](=[O:24])[NH:20][C:11]2[C:10]([C:8]=1[C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:25][CH3:26])=[CH:15][C:14]([C:16]([F:18])([F:17])[F:19])=[CH:13][CH:12]=2

Participants

4

Reactant 2

HCID 1049PyridineHCID 21834083HCID 21834083, compound

Product 1

HCID 154631583-Amino-4-(5-chloro-2-methoxyphenyl)-6-(trifluoromethyl)quinolin-2(1H)-oneYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mechanically stirred solution of N-[2-[(5-chloro-2-methoxyphenyl)carbonyl]-4-(trifluoromethyl)phenyl]chloroacetamide (12.2 g, 0.03 mol) in anhydrous pyridine (150 mL) was heated to reflux for 20-25 min. The resultant suspension of the pyridinium salt was allowed to cool and then diluted with benzene (100 mL). The pyridinium salt was filtered, washed with benzene and then dried in vacuo to afford the desired titled compound (13.75 g, 98%): mp 325-330° C. (dec.); IR (KBr, cm-1) 1678,1322,1270,1118; 1H NMR (300 MHz, DMSO-d6)δ 3.59 (3H, s), 7.09 (1H, d, J=9.0 Hz), 7.38 (1H, s), 7.44 (1H, d, J=2.6 Hz), 7.52 (1H, dd, J=8.9 and 2.6 Hz), 7.83 (1H, d, J=8.7 Hz), 8.11 (1H, dd, J=8.7 and 1.8 Hz), 8.19-8.27 (2H, m), 8.70-8.75 (1H, m), 9.05-9.07 (2H, m), 13.54 (1H, brd s); MS m/e 431 (MH)+.

Workup

  1. temperatureto reflux for 20-25 min
  2. temperatureto cool
  3. filtrationThe pyridinium salt was filtered
  4. washwashed with benzene
  5. customdried in vacuo

Sources & evidence

ORD record
ord-feff0e1cc1204695961010da77bc0493
Source dataset
uspto-grants-1999_10
Patent number
US05972961

Reaction notes

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