Sodium Carbonate → 7-Benzyloxy-4-(4-chloro-2-fluoro-phenylamino)-6-methoxy-quinoline-3-carbonitrile

HRID 612218Notes

Reaction equation

HRID 612218 reaction equation
C(OC1C=C2C(C(Cl)=C(C#N)C=N2)=CC=1OC)C1C=CC=CC=1.ClC1C=CC(N)=C(F)C=1.Cl.N1C=CC=CC=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH2:53]([O:60][C:61]1[CH:70]=[C:69]2[C:64]([C:65]([NH:73][C:74]3[CH:79]=[CH:78][C:77]([Cl:80])=[CH:76][C:75]=3[F:81])=[C:66]([C:71]#[N:72])[CH:67]=[N:68]2)=[CH:63][C:62]=1[O:82][CH3:83])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>O>[CH2:53]([O:60][C:61]1[CH:70]=[C:69]2[C:64]([C:65]([NH:73][C:74]3[CH:79]=[CH:78][C:77]([Cl:80])=[CH:76][C:75]=3[F:81])=[C:66]([C:71]#[N:72])[CH:67]=[N:68]2)=[CH:63][C:62]=1[O:82][CH3:83])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

8

Reactant 6

HCID 10340Sodium CarbonateHCID 938984-Chloro-2-fluoroanilineHCID 101298981-EthoxyethanolHCID 10176127Pyridinium chlorideHCID 224666467-(Benzyloxy)-4-chloro-6-methoxyquinoline-3-carbonitrileHCID 224666887-Benzyloxy-4-(4-chloro-2-fluoro-phenylamino)-6-methoxy-quinoline-3-carbonitrile hydrochloride

Product 1

HCID 224666897-Benzyloxy-4-(4-chloro-2-fluoro-phenylamino)-6-methoxy-quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.200 g of 7-benzyloxy-4chloro-6-methoxy-quinoline-3-carbonitrile 0.108 g of 4-chloro-2-fluoroaniline, 0.071 g of pyridine hydrochloride, and 3 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 1 h. The mixture was cooled and added to 10 ml of water. To this mixture was added sodium carbonate until pH 9. The product was collected, washed with water, and dried to give 0. 150 g of 7-Benzyloxy-4-(4-chloro-2-fluoro-phenylamino)-6-methoxy-quinoline-3-carbonitrile hydrochloride as a solid, mp 241-243° C.; mass spectrum (electrospray, m/e): M+H 433.9.

Workup

  1. temperatureat reflux temperature for 1 h
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried
  6. customto give 0

Sources & evidence

ORD record
ord-aaf785854450436bb573c4cfea0c7a5e
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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