3-Bromoaniline → HCID 22466609, compound

HRID 612182Notes

Reaction equation

HRID 612182 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].Cl.N1C=CC=CC=1>C(OCCO)C>[Br:16][C:17]1[CH:18]=[C:19]([NH:20][C:2]2[C:11]3[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[C:14]#[N:15])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 10176127Pyridinium chlorideHCID 224666994-Chloro-8-methoxyquinoline-3-carbonitrile

Product 1

HCID 22466609HCID 22466609, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 328.0 mg (1.5 mmol) of 4-chloro-8-methoxy -3-quinolinecarbonitrile, 309.7 mg (1.8 mmol) of 3-bromoaniline and 173.3 mg (1.5 mmol) of pyridine hydrochloride in 15 ml of 2-ethoxyethanol was refluxed under nitrogen for 0.5 hours. The solvent was removed and the residue was diluted with water followed by neutralization to pH 7-8 with diluted sodium carbonate solution. The precipitate was collected and washed with ether and dried in vacuo to give 476.1 mg (89.6%) of the product as a yellow solid, m.p. 210-212° C.; mass spectrum (electrospray, m/e): M+H 353.8, 355.8.

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with water
  3. customThe precipitate was collected
  4. washwashed with ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b8b01c2340864c469dd21379ef6b3a13
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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