Water → 6-[2-(4-Methoxy-2-nitrophenyl)hydrazinylidene]-3-[3-(trimethylsilyl)propoxy]cyclohexa-2,4-dien-1-one

HRID 377528Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=2[OH:18])=[C:5]([N+:19]([O-:21])=[O:20])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])=[CH:13][C:12]=2[OH:18])=[C:5]([N+:19]([O-:21])=[O:20])[CH:4]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 4-(4-methoxy-2-nitrophenylazo)benzene-1,3-diol (2.5 g, i.e. 0.0086 mol) and potassium carbonate (1.24 g) in 30 ml of dimethylformamide was brought to 70-75° C. 3-Chloropropyltrimethylsilane (1.24 g, i.e. 0.0086 mol) was added thereto over 20 minutes. The mixture was stirred at 75° C. for 6 hours. The reaction mixture was then poured into 50 ml of water and extracted with diisopropyl ether. The organic phase was dried, concentrated and purified by column chromatography (eluent: 50/50 heptane/CH2Cl2) to give compound (9) in the form of a red powder.

Workup

customwas brought to 70-75° C
extractionextracted with diisopropyl ether
customThe organic phase was dried
concentrationconcentrated
custompurified by column chromatography (eluent: 50/50 heptane/CH2Cl2)

Sources & evidence

ORD record: ord-a1a0dcf316584d059517a64345bc6920
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06027537

Reaction notes

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