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

HRID 1935129Notes

Reaction equation

HRID 1935129 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:21])=[C:14]([C:19]#[N:20])[CH:15]=[N:16]2)=[CH:11][C:10]=1[O:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[C:27]([F:32])[CH:26]=1.Cl.N1C=CC=CC=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[ClH:21].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:29][C:28]3[CH:30]=[CH:31][C:25]([Cl:24])=[CH:26][C:27]=3[F:32])=[C:14]([C:19]#[N:20])[CH:15]=[N:16]2)=[CH:11][C:10]=1[O:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 938984-Chloro-2-fluoroanilineHCID 101298981-EthoxyethanolHCID 10176127Pyridinium chlorideHCID 224666467-(Benzyloxy)-4-chloro-6-methoxyquinoline-3-carbonitrile

Product 1

HCID 224666887-Benzyloxy-4-(4-chloro-2-fluoro-phenylamino)-6-methoxy-quinoline-3-carbonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.200 g of 7-benzyloxy-4-chloro-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

Sources & evidence

ORD record
ord-8123a8b2d42a43a1a29dacbf31aa2836
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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