Sodium Carbonate → 4-(3-Bromo-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrile

HRID 612156Notes

Reaction equation

HRID 612156 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[Br:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24].C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[Br:20][C:21]1[CH:22]=[C:23]([NH:24][C:2]2[C:11]3[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:18]#[N:19])[CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 115623-BromoanilineHCID 101298981-EthoxyethanolHCID 224666114-Chloro-6,7,8-trimethoxy-3-quinolinecarbonitrile

Product 1

HCID 224665814-(3-Bromo-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrileYield 85.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.167 g of 4-chloro-6,7,8-trimethoxy-3-quinolinecarbonitrile, 0.12 g of m-bromoaniline, and 5 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 30 minutes. The mixture was cooled and added to 50 ml of water. To this mixture was added sodium carbonate to pH 9. The product was collected, washed with water, dried, and washed with 10 ml of hexanes-ethyl acetate (4:1) to give 0.212 g of 4-(3-bromo-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrile as a solid, mp 211-213° C.; mass spectrum (EI, m/e): M 413.0377.

Workup

  1. temperatureat reflux temperature for 30 minutes
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried
  6. washwashed with 10 ml of hexanes-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-372373975a704d44b92d5be576a30e23
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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