3-Bromoaniline → HCID 18548941, compound

HRID 276876Notes

Reaction equation

HRID 276876 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>C(O)C.CCOCC>[Br:15][C:16]1[CH:17]=[C:18]([NH:19][C:2]2[C:11]3[C:6](=[CH:7][N:8]=[C:9]([Cl:12])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:13]#[N:14])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 115623-BromoanilineHCID 185489614,6-Dichloro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 18548941HCID 18548941, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To the above 600 mg of 4,6-dichloro-[1.7]naphthyridine-3-carbonitrile in 20 mL of absolute ethanol was added 1 mL of 3-bromoaniline. After refluxing the reaction under an inert atmosphere for 4 hours, the reaction mixture was cooled to ambient temperature, diluted with ether, and the product was filtered and washed with ether. Drying in vacuo yielded 790 mg of 4-(3-bromo-phenylamino)-6-chloro-[1.7]naphthyridine-3-carbonitrile as an off-white solid: mp=220-223° C.; mass spectrum (m/e): M+H 359.0, 361.1.

Workup

  1. temperatureAfter refluxing
  2. customthe reaction under an inert atmosphere for 4 hours
  3. filtrationthe product was filtered
  4. washwashed with ether
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-453d6e198bc24996bb23486f5aefab8c
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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