3-Bromoaniline → HCID 5328873, compound

HRID 612047Notes

Reaction equation

HRID 612047 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([O:12][CH2:13][CH3:14])[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-])(O)=O.[Na+]>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:15][CH3:16])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:17]#[N:18])[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 516892Sodium BicarbonateHCID 10539447HCID 10539447, compound

Product 1

HCID 5328873HCID 5328873, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.00 g (3.82 mmol) of 4-chloro-6-ethoxy-7-methoxyquinoline-3-carbonitrile and 0.788 g (4.58 mmol) of 3-bromoaniline in 20 mL of ethanol was refluxed under N2 for 7 h. Saturated NaHCO3 was added, volatile material was removed and the residue was azeotroped with ethanol. The crude product was slurried with hexane, filtered, washed with water and dried. Recrystallization from ethanol gave 1.31 g of 4(3-bromophenylamino)-6-ethoxy-7-methoxyquinoline-3-carbonitrile as tan crystals: mass spectrum (electrospray, m/e): M+H 397.9, 399.8.

Workup

  1. temperaturewas refluxed under N2 for 7 h
  2. customvolatile material was removed
  3. customthe residue was azeotroped with ethanol
  4. filtrationfiltered
  5. washwashed with water
  6. customdried
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-1488ee165da549ee8bc88b6883872815
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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