Dichloromethane → HCID 54408222, compound

HRID 1376484Notes

Reaction equation

HRID 1376484 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:11]([CH:19]=[C:20]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[C:21]#[N:22])[C:10]2=[O:29])=[CH:5][CH:4]=1.CC=C(C)C.B(Br)(Br)Br.ClCCl>C(Cl)(Cl)Cl.O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:11]([CH:19]=[C:20]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[C:21]#[N:22])[C:10]2=[O:29])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 105532-Methyl-2-buteneHCID 25134Boron tribromideHCID 53725431HCID 53725431, compound

Product 1

HCID 54408222HCID 54408222, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
-40 °C

Procedure

2.5 g of 3-[1,2-dihydro-1-(4-methoxyphenyl)-2-oxo-1,8-naphthyridin-3-yl]-2-(3-pyridyl)prop-2-enenitrile, prepared in Example 82, are dissolved in 100 ml of chloroform stabilized with amylene. The yellow solution is cooled to -40° C. and 13.2 ml of a 1 M solution of BBr3 in dichloromethane (2 eq) are then added dropwise at this temperature, with stirring. The mixture is then left to warm up to room temperature and stirring is continued for 15 h. The reaction medium is hydrolyzed by the addition of 100 ml of water, after which the aqueous phase is separated off and extracted several times with dichloromethane. The precipitate which appears is filtered off, washed with acetone and dried to give 0.21 g of 3-[1,2-dihydro-1-(4-hydroxy- phenyl)-2-oxo-1,8-naphthyridin-3-yl]-2-(3-pyridyl)prop-2-enenitrile in the form of a yellow solid melting at >317° C. Yield 9%.

Workup

  1. waitThe mixture is then left
  2. temperatureto warm up to room temperature
  3. stirringstirring
  4. customafter which the aqueous phase is separated off
  5. extractionextracted several times with dichloromethane
  6. filtrationThe precipitate which appears is filtered off
  7. washwashed with acetone
  8. customdried

Sources & evidence

ORD record
ord-fe571bb0d3ca483a9a97e2d301ca0ec7
Source dataset
uspto-grants-1997_09
Patent number
US05663181

Reaction notes

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