Dichloromethane → HCID 22241259, compound

HRID 892161Notes

Reaction equation

HRID 892161 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[CH:4]=[C:3]1[CH2:13]O.P(Br)(Br)[Br:16].C(Cl)Cl>CN(C=O)C>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[CH:4]=[C:3]1[CH2:13][Br:16]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24614Phosphorus tribromide2×HCID 157330182-(Hydroxymethyl)-1-methylquinolin-4(1H)-one

Product 1

HCID 22241259HCID 22241259, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-methyl-4-oxo-1,4-dihydroquinolin-2-ylmethanol (112 mg, 0.592 mmoles, Coppola, G. M. J. Heterocyclic Chem., 1986, 23, 1717) and phosphorous tribromide (56.2 uL, 0.592 mmoles) in 3:1 CH2Cl2: DMF (20 mL) is stirred 18 hours and another portion (20 mL) of phosphorous tribromide is added. After 24 hours distilled water (10 mL) is added and extracted with EtOAc. The organic layer is concentrated and the resulting residue purified by column chromatography (silica, 20:1 CH2Cl2:MeOH) to yield the title compound as a white solid. MS (ESI) 252, 254 (M+H)+, Br pattern.

Workup

  1. distillationAfter 24 hours distilled water (10 mL)
  2. additionis added
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer is concentrated
  5. customthe resulting residue purified by column chromatography (silica, 20:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-53ed94e8c6834ad08b3287ad68675245
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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