Dichloromethane → HCID 18969127, compound

HRID 398837Notes

Reaction equation

HRID 398837 reaction equation
B(Br)(Br)Br.ClCCl.C[O:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH3:26])[C:18](=[O:27])[CH:17]=2)[CH:13]=[CH:14][CH:15]=1>CO>[OH:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH3:26])[C:18](=[O:27])[CH:17]=2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 18969151HCID 18969151, compound

Product 1

HCID 18969127HCID 18969127, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 M-dichloromethane solution of boron tribromide (25 ml, 25 mmol) was added to a dichloromethane solution (30 ml) of 4-(3-methoxyphenyl)-1-methyl-1,8-naphthyridin-2(1H)-one (1.3 g, 4.9 mmol) at -35° C., and the mixture was gradually warmed up to room temperature and then stirred at room temperature for 2 hours. Methanol (10 ml) was added to the reaction solution at -60° C., and the mixture was warmed up to room temperature and then stirred at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure, methanol (30 ml) was added to the residue, and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (benzene-ethyl acetate) to give 4-(3-hydroxyphenyl)-1-methyl-1,8-naphthyridin-2(1H)-one (0.29 g, 23%).

Workup

  1. temperaturethe mixture was warmed up to room temperature
  2. stirringstirred at room temperature for 30 minutes
  3. concentrationThe reaction solution was concentrated under reduced pressure, methanol (30 ml)
  4. additionwas added to the residue
  5. concentrationthe mixture was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (benzene-ethyl acetate)

Sources & evidence

ORD record
ord-c4bf48181c70489c8bfd5e39a1719b4b
Source dataset
uspto-grants-1998_10
Patent number
US05817670

Reaction notes

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