Water → HCID 23369643, compound

HRID 1900781Notes

Reaction equation

HRID 1900781 reaction equation
[CH2:1]([C:4]1[C:13]([OH:14])=[CH:12][C:11]([CH3:15])=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:16])[NH:9]2)[CH:2]=[CH2:3].[Br:17]N1C(=O)CCC1=O.O.O1CCCC1>C(Cl)(Cl)Cl>[Br:17][CH2:3][CH:2]1[O:14][C:13]2[C:4](=[C:5]3[C:10](=[C:11]([CH3:15])[CH:12]=2)[NH:9][C:8](=[O:16])[CH:7]=[CH:6]3)[CH2:1]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 23369736HCID 23369736, compound2×

Product 1

HCID 23369643HCID 23369643, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-Allyl-6-hydroxy-8-methylcarbostyril (9.36 g, 43.5 mmol) was dissolved in chloroform (11) with heat. To the obtained solution, N-bromosuccinimide (7.75 g, 43.5 mmol) was added, and the mixture was refluxed for 2 hours. After completion of the reaction, water was added to the reaction mixture, and unreacted 5-allyl-6-hydroxy-8-methylcarbostyril (2.2 g, 23.5%) was separated as an insoluble matter by filtration. The filtrate was washed with water, dried and condensed. The resultant residue was subjected to a recrystallizing procedure using tetrahydrofuran to obtain 4.90 g of 2-bromomethyl-5-methyl-1,2-dihydrofuro-[3,2-f]quinoline-7-one as pale yellow crystals (38.3%).

Workup

  1. temperaturewith heat
  2. temperaturethe mixture was refluxed for 2 hours
  3. customwas separated as an insoluble matter by filtration
  4. washThe filtrate was washed with water
  5. customdried
  6. customcondensed

Sources & evidence

ORD record
ord-ae36c676b2e143b6ac13ff0f49573bbc
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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