Sodium Hydroxide → 4-[3-(1H-Tetrazol-5-yl)phenyl]-1,4-dihydrobenzo[f]quinoxaline-2,3-dione

HRID 1186722Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:18]3[CH:17]=[CH:16][C:15]4[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=4[C:13]=3[NH:12][C:11](=[O:23])[C:10]2=[O:24])[CH:6]=[CH:7][CH:8]=1)#[N:2].C([Sn]([N:38]=[N+:39]=[N-:40])(CCCC)CCCC)CCC.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH:38]1[C:1]([C:3]2[CH:4]=[C:5]([N:9]3[C:18]4[CH:17]=[CH:16][C:15]5[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=5[C:13]=4[NH:12][C:11](=[O:23])[C:10]3=[O:24])[CH:6]=[CH:7][CH:8]=2)=[N:2][N:40]=[N:39]1

Participants

Conditions

Temperature: 110 °C

Procedure

To an anhydrous toluene (1 mL)-anhydrous DMF (1.5 mL) solution of 4-(3-cyanophenyl)-1,4-dihydrobenzo[f]quinoxaline-2,3-dione (20 mg, 0.064 mmol) was added tri-n-butyltin azide (53 μL, 0.192 mmol), and the mixture was stirred at 110° C. for 18 hours. After cooling on standing, the reaction mixture was poured into a 1M aqueous sodium hydroxide solution, and washed with ethyl acetate. After neutralization of the aqueous layer by addition of a 1M aqueous hydrochloric acid solution, the precipitated solid was collected by filtration, washed with water, and dried to obtain the titled compound as a white crystal (15 mg, yield 66%).

Workup

temperatureAfter cooling
washwashed with ethyl acetate
additionAfter neutralization of the aqueous layer by addition of a 1M aqueous hydrochloric acid solution
filtrationthe precipitated solid was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-488da16e13134109b19973b4fb3aab6f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673915B2

Reaction notes

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