N-Methylaniline → 2-Aminoquinoline

HRID 1850024Notes

Reaction equation

HRID 1850024 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[CH:6]=[CH:5]2.C[NH:14]C1C=CC=CC=1>>[NH2:14][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[CH:2][CH:3]=2)[N:8]=1

Participants

3

Reactant 2

HCID 7515N-MethylanilineHCID 128940866-Bromo-2-chloroquinoline

Product 1

HCID 113792-Aminoquinoline

Procedure

6-Bromo-2-chloroquinoline (250 mg, 1.0 mmol) and N-methylaniline (2 mL) were heated at 120° C. for 16 hours. Extraction from 2M NaOH into DCM and drying on Na2SO4 gave the crude 2-aminoquinoline. This was converted, via Methods 3 and 5, to compound 205 (88 mg, 31%). [M−H]−=277.0 m/z. Activity: B

Workup

  1. extractionExtraction from 2M NaOH into DCM
  2. customdrying on Na2SO4

Sources & evidence

ORD record
ord-3bc8e453fa27474196bab6253a9b597d
Source dataset
uspto-grants-2015_02
Patent number
US08957049B2

Reaction notes

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