3-Bromoaniline → HCID 11144112, compound

HRID 548447Notes

Reaction equation

HRID 548447 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[Br:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24].C(=O)(O)[O-].[Na+]>C(O)C>[Br:20][C:21]1[CH:22]=[C:23]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:18]#[N:19])[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 516892Sodium BicarbonateHCID 110113054-Chloro-7-ethoxy-6-nitroquinoline-3-carbonitrile

Product 1

HCID 11144112HCID 11144112, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.1 g (7.6 mmol) of 4-chloro-7-ethoxy-6-nitro-quinoline-3-carbonitrile and 0.91 ml (8.3 mmol) of 3-bromo aniline in 100 ml ethanol was refluxed under nitrogen for 4.5 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 sulfate. The solution was concentrated and solid was collected and then washed with hexane. Upon drying, 2.6 g of yellow solid obtained: mass spectrum (electrospray, m/e) M+H 412.8 and 414.9.

Workup

  1. temperaturewas refluxed under nitrogen for 4.5 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 sulfate
  6. concentrationThe solution was concentrated
  7. customsolid was collected
  8. washwashed with hexane
  9. customUpon drying

Sources & evidence

ORD record
ord-5acda4f97a5b45f196bb75a13e2d6165
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

Loading…