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Dimethylformamide → 7-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-2-(1H-tetrazol-5-yl)-chromen-4-one

HRID 1090777
Notes
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Reaction equation

HRID 1090777 reaction equation
[C:1]([C:3]1[O:4][C:5]2[CH:13]=[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]4[CH:33]=[CH:32][C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]=4)[CH:17]=3)[CH:11]=[CH:10][C:6]=2[C:7](=[O:9])[CH:8]=1)#[N:2].[N-:34]=[N+:35]=[N-:36].[Na+].Cl.N1C=CC=CC=1.CN(C)C=O>O>[N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[CH:33][C:24]=1[CH2:23][O:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][O:14][C:12]1[CH:11]=[CH:10][C:6]2[C:7](=[O:9])[CH:8]=[C:3]([C:1]3[NH:36][N:35]=[N:34][N:2]=3)[O:4][C:5]=2[CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 10176127Pyridinium chlorideHCID 148423662-cyano-7-(3-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H-1-benzopyran

Product 1

HCID 1785158027-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-2-(1H-tetrazol-5-yl)-chromen-4-one

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
100 °C

Procedure

2-cyano-7-(3-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H-1-benzopyran (2.97 mmoles), sodium azide (965 mg), pyridine hydrochloride (1.72g) and dimethylformamide (7 ml) are combined and heated at 100° C. for 48 hours. The reaction mixture is poured into cold water and the resulting precipitate is collected. The precipitate is dissolved in hot ethanol and reprecipitated by addition of water to give 5-(7-(3-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H-1-benzopyran-2-yl)tetrazole which decomposes at 203° C.

Workup

  1. customthe resulting precipitate is collected
  2. dissolutionThe precipitate is dissolved in hot ethanol
  3. customreprecipitated by addition of water

Sources & evidence

ORD record
ord-aecca7751ee947558a719fd9f6d9ed46
Source dataset
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05082849

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes