Bromine → 4-Chloroquinolin-2-amine

HRID 1829157Notes

Reaction equation

HRID 1829157 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-7e57fc38a5d046a9aad76fd77852972d
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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