3-Bromoaniline → HCID 11811432, compound

HRID 1935058Notes

Reaction equation

HRID 1935058 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:15][CH3:16])[CH:8]=[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+]>C(O)C>[N+:12]([C:9]1[CH:10]=[C:11]2[C:6](=[C:7]([O:15][CH3:16])[CH:8]=1)[N:5]=[CH:4][C:3]([C:17]#[N:18])=[C:2]2[NH:23][C:22]1[CH:24]=[CH:25][CH:26]=[C:20]([Br:19])[CH:21]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 516892Sodium BicarbonateHCID 11129151HCID 11129151, compound

Product 1

HCID 11811432HCID 11811432, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.9 g (7.6 mmol) of 4-chloro-8-methoxy-6-nitro-quinoline-3-carbonitrile and 0.86 ml (8.3 mmol) of 3-bromo aniline in 95 ml ethanol was refluxed under nitrogen for 5 hours. The reaction mixture was poured into diluted sodium bicarbonate solution. Ethanol was removed under vacuum. The mixture was diluted with ethyl acetate and the organic layer was separated and dried over sodium chloride. The solution was concentrated and solid was collected and then washed with hexane. Upon drying, 2.3 g of yellow solid obtained: mass spectrum (electrospray, m/e) M+H 398.8 and 400.8.

Workup

  1. temperaturewas refluxed under nitrogen for 5 hours
  2. customEthanol was removed under vacuum
  3. additionThe mixture was diluted with ethyl acetate
  4. customthe organic layer was separated
  5. dry with materialdried over sodium chloride
  6. concentrationThe solution was concentrated
  7. customsolid was collected
  8. washwashed with hexane
  9. customUpon drying

Sources & evidence

ORD record
ord-e977e41b11e749e3a454cd0c56032507
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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