Sodium Azide → HCID 23369615, compound

HRID 1900815Notes

Reaction equation

Br[CH2:2][C:3]1([CH3:19])[O:18][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[C:9]([CH3:17])=[CH:8]3.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[N:20]([CH2:2][C:3]1([CH3:19])[O:18][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[C:9]([CH3:17])=[CH:8]3)=[N+:21]=[N-:22]

Participants

Conditions

Temperature: 150 °C

Procedure

To 2-bromomethyl-2,5,8-trimethyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (3.93 g, 12.2 mmol) and sodium azide (5.15 g, 79.3 mmol), dimethylformamide (85 ml) was added, and the mixture was stirred for 3 hours in a bath at 150° C. After cooling, post-treatment and recrystallization (chloroform-n-hexane) were performed in a manner similar to that described in Example 278 to obtain 3.28 g of the title compound as colorless crystals (94.7%).

Workup

temperatureAfter cooling
customrecrystallization (chloroform-n-hexane)

Sources & evidence

ORD record: ord-72e469a2d9ba4ac6b09ac070e202f158
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576324

Reaction notes

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