Water → HCID 89852229, compound

HRID 530215Notes

Reaction equation

HRID 530215 reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=2)[N:3]=1.[O:17]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(O)C>[N+:14]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[CH:2][C:11]([C:12]#[N:13])=[C:10]2[NH:28][C:27]1[CH:26]=[CH:25][C:24]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:30][CH:29]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 8764(4-Aminophenoxy)benzeneHCID 89853528HCID 89853528, compound

Product 1

HCID 89852229HCID 89852229, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of -chloro-6-nitroquinoline-3-carbonitrile (4.1 g, 17.6 mmol, 1.0 eq), 4-phenoxyaniline (2.6 g, 14.1 mmol, 0.8 eq) was dissolved in ethanol (40 mL). The reaction was heated to reflux for 2 hours, cooled to room temperature, poured into water (50 mL), and washed with ethyl acetate (50×2 mL). It was filtrated and dried in vacuum to give 6-nitro-4-((4-phenoxyphenyl)amino)quinoline-3-carbonitrile (Compound 18) as a solid (5.6 g)

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. washwashed with ethyl acetate (50×2 mL)
  4. filtrationIt was filtrated
  5. customdried in vacuum

Sources & evidence

ORD record
ord-a2e0bac7d13c4fb092ce7e23ec954c25
Source dataset
uspto-grants-2016_05
Patent number
US09353062B2

Reaction notes

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