3-Bromoaniline → 4-(3-Bromo-phenylamino)-6-nitro-[1,8]naphthyridine-3-carbonitrile

HRID 1266257Notes

Reaction equation

HRID 1266257 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21]>C(O)(C)C>[Br:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[C:6](=[N:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 155506564-Chloro-6-nitro-1,8-naphthyridine-3-carbonitrile

Product 1

HCID 99292724-(3-Bromo-phenylamino)-6-nitro-[1,8]naphthyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 7.5 g (32 mmol) of 4-chloro-6-nitro-[1.8]naphthyridine-3-carbonitrile and 5.5 g (32 mmol) of 3-bromo-aniline in 175 ml of isopropanol was stirred at reflux for 2 hr. and 45 min. The mixture was cooled, solid was collected, and washed with ether giving 12.9 g of the title compound as the yellow hydrochloride salt: mass spectrum (electrospray, m/e): M+H 370, 373.

Workup

  1. temperatureat reflux for 2 hr
  2. custom45 min
  3. temperatureThe mixture was cooled
  4. customsolid was collected
  5. washwashed with ether giving 12.9 g of the title compound as the yellow hydrochloride salt

Sources & evidence

ORD record
ord-e9e2c83f9d2747458b5c3173c7cee110
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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