Dimethylformamide → HCID 23369700, compound

HRID 1900782Notes

Reaction equation

HRID 1900782 reaction equation
Br[CH2:2][CH:3]1[O:15][C:14]2[C:5](=[C:6]3[C:11](=[C:12]([CH3:16])[CH:13]=2)[NH:10][C:9](=[O:17])[CH:8]=[CH:7]3)[CH2:4]1.[N-:18]=[N+:19]=[N-:20].[Na+].CN(C)C=O>C(Cl)(Cl)Cl>[N:18]([CH2:2][CH:3]1[O:15][C:14]2[C:5](=[C:6]3[C:11](=[C:12]([CH3:16])[CH:13]=2)[NH:10][C:9](=[O:17])[CH:8]=[CH:7]3)[CH2:4]1)=[N+:19]=[N-:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 23369643HCID 23369643, compound

Product 1

HCID 23369700HCID 23369700, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromomethyl-5-methyl-1,2-dihydrofuro-[3,2-f]quinoline7-one (4.90 g, 16.7 mmol) and sodium azide (7.5 g, 115 mmol) were added to dimethylformamide (150 ml), and the mixture was stirred in a bath of 100° C. for 1.5 hours, followed by cooling and condensing. The residue was combined with chloroform, and washed with water. The washed material was dried and condensed. The resultant residue was recrystallized from chloroform--n-hexane. As a result, 4.12 g of 2-azidomethyl-5-methyl-1,2-dihydrofuro-[3,2-f]quinoline-7-one was obtained as brown prisms (96.6%).

Workup

  1. temperatureby cooling
  2. customcondensing
  3. washwashed with water
  4. customThe washed material was dried
  5. customcondensed
  6. customThe resultant residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-497481082c6f47618b8a0cc9bcd25f8b
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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