3-Bromoaniline → 4-(3-Bromophenylamino)-7-ethoxy-6-methoxyquinoline-3-carbonitrile

HRID 1935028Notes

Reaction equation

HRID 1935028 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH3:16])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[Br:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23]>C(O)C>[Br:19][C:20]1[CH:21]=[C:22]([NH:23][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][CH3:16])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:17]#[N:18])[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 105634734-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile

Product 1

HCID 53288744-(3-Bromophenylamino)-7-ethoxy-6-methoxyquinoline-3-carbonitrileYield 73.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 500 mg (1.90 mmol) 4-chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile, 20 ml ethanol, and 250 μl (2.28 mmol) 3-bromoaniline was heated to reflux under N2. At 3 hours, added 103 μl (0.95 mmol) and 10 ml ethanol and refluxed overnight. Removed heat and made basic with saturated sodium bicarbonate. Stripped solvent, slurried residue with hexane, collected solids, and dried. Washed with water and dried in vacuo, giving 554 mg of tan solid: mass spectrum (electrospray m/e): M+H=398, 399.8.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. temperaturerefluxed overnight
  4. customRemoved
  5. temperatureheat
  6. customcollected solids
  7. customdried
  8. washWashed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-ce026893302c437385ada0046ada3bec
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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