Hydrochloric Acid → HCID 178526907, compound

HRID 1646365Notes

Reaction equation

[C:1]([C:3]1[CH:22]=[CH:21][C:6]([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[N:10]([CH3:20])[CH:9]=2)=[C:5]([O:23][CH3:24])[CH:4]=1)#[N:2].[N-:25]=[N+:26]=[N-:27].[Na+].Cl.C([N:32]([CH2:35]C)CC)C.Cl>CN1CCCC1=O>[CH3:24][O:23][C:5]1[CH:4]=[C:3]([C:1]2[NH:27][N:26]=[N:25][N:2]=2)[CH:22]=[CH:21][C:6]=1[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=2)[N:10]([CH3:20])[CH:9]=1.[N+:17]([C:35]1[NH:32][N:27]=[N:26][N:25]=1)([O-:19])=[O:18]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 3-(4-cyano-2-methoxybenzyl)-1-methyl-5-nitroindole (0.458 g.), sodium azide (0.741 g.), and triethylamine hydrochloride (0.785 g.) in dry N-methyl-2-pyrrolidinone (6 ml.), under nitrogen, was stirred and heated at 150° C. for 1.5 hours. The mixture was cooled to ambient temperature, 1N hydrochloric acid (25 ml.) added cautiously, while stirring, the precipitated solid isolated by filtration, washed with water and dried in vacuo to give 3-[2-methoxy-4-(1-H-tetrazol-5-yl)benzyl]-1-methyl-5nitroindole, (V) (0.484 g., 94%) as a yellow powder, m.p. 249°-250° C.: partial NMR (250 MHz, DMSO-d6): 3.82 (s,3 H, NMe): 3.97 (s,3 H, OMe); 4.13 (s,2 H, ArCH2).

Workup

temperatureThe mixture was cooled to ambient temperature
stirringwhile stirring
customthe precipitated solid isolated by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-edcb628d483a4b5780ff393638c7d00d
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05179112

Reaction notes

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