3-Bromoaniline → 4-[(3-Bromophenyl)amino]-7-methoxy-6-nitro-quinoline-3-carbonitrile

HRID 548408Notes

Reaction equation

HRID 548408 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([N+:12]([O-:14])=[O: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)(O)[O-].[Na+]>COC(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]([N+:12]([O-:14])=[O:13])[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 111399754-Chloro-7-methoxy-6-nitroquinoline-3-carbonitrile

Product 1

HCID 98438404-[(3-Bromophenyl)amino]-7-methoxy-6-nitro-quinoline-3-carbonitrileYield 15.3%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

A solution of 5.2 g (19.7 mmol) of 4-chloro-7-methoxy-6-nitro-quinoline-3-carbonitrile and 3.7 g (21.7 mmol) of 3-bromo aniline in 130 ml of methoxyethanol was refluxed under nitrogen for 4 hours. The reaction mixture was poured into dilute sodium bicarbonate solution. Solid was collected and washed with water and dried in air. The solid was chromatographed on silica gel eluting with chloroform-ethyl acetate 9:1. Solvent was removed from product fractions giving 1.2 g of 4-[(3-bromophenyl)amino]-7-methoxy-6-nitro-quinoline-3-carbonitrile as a yellow solid: mass spectrum (electrospray, m/e): M+H 399.0, 402.0.

Workup

  1. customSolid was collected
  2. washwashed with water
  3. customdried in air
  4. customThe solid was chromatographed on silica gel eluting with chloroform-ethyl acetate 9:1
  5. customSolvent was removed from product fractions

Sources & evidence

ORD record
ord-3360a26bf2de45268b8bbf969efd62cc
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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