4-Methoxybenzylamine → 6-Bromoquinolin-2-amine

HRID 2075707Notes

Reaction equation

HRID 2075707 reaction equation
[Br:1][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.COC1C=CC(C[NH2:20])=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH2:20])[CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 754524-MethoxybenzylamineHCID 128940866-Bromo-2-chloroquinoline

Product 1

HCID 111836666-Bromoquinolin-2-amine

Conditions

Temperature
140 °C

Procedure

6-Bromo-2-chloro-quinoline (3.34 g, 13.8 mmol) was dissolved in p-methoxybenzylamine (5 mL) and heated to 140° C. for 1 hour. The mixture was cooled to room temperature, filtered, and concentrated. The residue was purified by silica gel chromatography, and the isolated material was refluxed in TFA (6 mL) for 1 hour. The mixture was concentrated and purified by silica gel chromatography to give the desired product, 8a.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. temperaturethe isolated material was refluxed in TFA (6 mL) for 1 hour
  6. concentrationThe mixture was concentrated
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-4f9630e4ad174fb8a711a2bec6dbea5c
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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