Sodium Azide → 3-azido-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine

HRID 398785Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of sodium azide (0.55 g, 8.4 mmol) in DMSO (17 ml) was added 3-chloro-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine (1.6 g, 6.7 mmol) and the suspension was heated at 80° C. for 2.5 h. The hot reaction mixture was added on ice (30 g) and the precipitate was filtered and purified by chromatography on silica gel (200 g) using initially heptane as eluent and subsequently a mixture of heptane and ethyl acetate (1:1) to afford 1.1 g of 3-azido-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine.

Workup

additionThe hot reaction mixture was added on ice (30 g)
filtrationthe precipitate was filtered
custompurified by chromatography on silica gel (200 g)
additionsubsequently a mixture of heptane and ethyl acetate (1:1)

Sources & evidence

ORD record: ord-592d8e403ddf40d9914c4bcd64a64785
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05817654

Reaction notes

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