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Hydrochloric Acid → HCID 178526907, compound

HRID 275153
Notes
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Reaction equation

HRID 275153 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 233658773-(4-Cyano-2-methoxybenzyl)1-methyl-5-nitroindole

Product 2

HCID 178488254HCID 178488254, compoundHCID 178526907HCID 178526907, compound
Yield 590.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

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-5-nitroindole, (V) (0.484 g., 94%) as a yellow powder, m.p. 249°-250° C.; partial NMR (250 MHz, DMSO-d6): 3.82 (s,3H, NMe); 3.97(s,3H, OMe); 4.13(s,2H, ArCH2).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. stirringwhile stirring
  3. customthe precipitated solid isolated by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d4a685b6ca694f39a62c3774a83c4013
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05391758

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes