Bromine → HCID 57720101, compound

HRID 1985624Notes

Reaction equation

HRID 1985624 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9]3=[C:10]([CH2:17][CH2:18][CH2:19][N:8]3[CH:7]=1)[CH:11]=[CH:12][CH:13]=2)=[O:5])[CH3:2].[Br:20]Br>C(O)(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9]3=[C:10]([CH2:17][CH2:18][CH2:19][N:8]3[CH:7]=1)[CH:11]=[C:12]([Br:20])[CH:13]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 1531802HCID 1531802, compound

Product 1

HCID 57720101HCID 57720101, compoundYield 134.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To the solution of 1-Oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester (7.5 g, 29 mmol) in glacial acetic acid (120 mL) was added bromine (1.6 ml, 32 mmol). The mixture was stirred over night at room temperature, and new portion of bromine (1.6 mL, 32 mmol) was added. After 24 h, reaction mixture was diluted with 100 mL of H2O and pH was adjusted to 2.9. Precipitate was filtered and dried. The crude product was precipitated from CH2Cl2/Diisoprophylether and dried in vacuum drier yielding 13.07 g of the crude title product.

Workup

  1. customreaction mixture
  2. filtrationPrecipitate was filtered
  3. customdried
  4. customThe crude product was precipitated from CH2Cl2/Diisoprophylether
  5. customdried in vacuum drier

Sources & evidence

ORD record
ord-176ba45c106243309d565c08e1e8d6eb
Source dataset
uspto-grants-2009_06
Patent number
US07547679B2

Reaction notes

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