Dimethylformamide → HCID 23369764, compound

HRID 1900845Notes

Reaction equation

HRID 1900845 reaction equation
CN(C)C=O.Br[CH2:7][C:8]1([CH3:25])[O:24][C:11]2=[C:12]3[C:17](=[C:18]([CH3:20])[CH:19]=[C:10]2[CH2:9]1)[NH:16][C:15](=[O:21])[C:14]([CH2:22][CH3:23])=[CH:13]3.[N-:26]=[N+:27]=[N-:28].[Na+]>C(Cl)(Cl)Cl.CCCCCC>[N:26]([CH2:7][C:8]1([CH3:25])[O:24][C:11]2=[C:12]3[C:17](=[C:18]([CH3:20])[CH:19]=[C:10]2[CH2:9]1)[NH:16][C:15](=[O:21])[C:14]([CH2:22][CH3:23])=[CH:13]3)=[N+:27]=[N-:28]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 23369560HCID 23369560, compound

Product 1

HCID 23369764HCID 23369764, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 21585165Chloroform hexaneSolvent

Procedure

Dimethylformamide (21 ml) was added to a mixture of 2-bromomethyl-8-ethyl-2,5-dimethyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (920 mg, 2.74 mmol) and sodium azide (1.30 g, 19.9 mmol). The procedure of Example 278 was followed (reaction, post-treatment, and recrystallization from chloroform-n-hexane) to obtain 740 mg of the title compound as colorless needles (80.9%).

Sources & evidence

ORD record
ord-d3aa1d1fcb41407c8217096e8d60c7ae
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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