Bromine → 4-Chloroquinolin-2-amine

HRID 1791948Notes

Reaction equation

HRID 1791948 reaction equation
BrBr.[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6](C(N)=O)[CH:5]=1.Cl.Cl.Cl.COC(C1C=C(N2CCN([C@@H]3CN[C@H](C(N4CCSC4)=O)C3)CC2)C2C(=CC=CC=2)[N:25]=1)=O>[OH-].[K+].O1CCCC1>[NH2:25][C:6]1[CH:5]=[C:4]([Cl:3])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 220292874-Chloro-2-quinolinecarboxamideHCID 67508184HCID 67508184, compound

Product 1

HCID 140674074-Chloroquinolin-2-amine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14797Potassium HydroxideSolvent

Procedure

Bromine (2.32 mL) was dissolved in 5% aqueous potassium hydroxide solution (190 mL), and a solution of 4-chloroquinoline-2-carboxamide [product of Example 262 (1), 9.80 g] in tetrahydrofuran (190 mL) was dropwise added thereto. The mixture was stirred at room temperature for 30 min, and the mixture was stirred at 80° C. for 1 hr with heating. The reaction mixture was filtrated and the filtrate was added to water. The mixture was extracted with chloroform, and the extract was washed with brine and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 2-amino-4-chloroquinoline (1.98 g) as a pale-yellow solid.

Workup

  1. stirringthe mixture was stirred at 80° C. for 1 hr
  2. temperaturewith heating
  3. filtrationThe reaction mixture was filtrated
  4. additionthe filtrate was added to water
  5. extractionThe mixture was extracted with chloroform
  6. washthe extract was washed with brine
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ce7bfe590e3a4a64a00c07b68f3053f5
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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