Aniline → HCID 68183224, compound

HRID 513808Notes

Reaction equation

HRID 513808 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:8]([C:11]1[C:12](Cl)=[CH:13][CH:14]=[C:15]2[C:20]=1[N:19]=[CH:18][CH:17]=[CH:16]2)([O-:10])=[O:9]>N1C=CC=CC=1.CCOC(C)=O>[N+:8]([C:11]1[C:12]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:14]=[C:15]2[C:20]=1[N:19]=[CH:18][CH:17]=[CH:16]2)([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 6115AnilineHCID 4597147-Chloro-8-nitroquinoline

Product 1

HCID 68183224HCID 68183224, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

Aniline (2 ml, 21 mmol) was added to a solution of 8-nitro-7-chloroquinoline 40 (200 mg, 0.96 mmol) in pyridine (1 ml) and the mixture was heated in a microwave at 170° C. under nitrogen for 3 h. The residue was dissolved in EtOAc (50 ml) and the organic phase was washed with sat. NaHCO3 (30 ml) and concentrated in vacuo to give the title compound (230 mg, 89%) which was used in the next step without further purification.

Workup

  1. washthe organic phase was washed with sat. NaHCO3 (30 ml)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04bce721b6b8469e84a06ec94b7c182e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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