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

HRID 611976Notes

Reaction equation

HRID 611976 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 4chloro-7-methoxy-6-nitro-3-quinolinecarbonitrile 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-3-quinolinecarbonitrile 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-e9fa3bcffc4e43e1b50065d308fef0c7
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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