Toluene → HCID 68700177, compound

HRID 1437373Notes

Reaction equation

HRID 1437373 reaction equation
[CH:1]([Si:4]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[C:7]=1[NH2:13])([CH3:3])[CH3:2].[C:20](OCC)(=O)[CH:21]=[O:22].C1(C)C=CC=CC=1>C(O)C>[CH:17]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:14]([CH3:16])[CH3:15])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:7]=1[N:13]=[CH:20][C:21](=[O:22])[NH:12]2)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 68701552HCID 68701552, compound

Product 1

HCID 68700177HCID 68700177, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (b) (80.7 g) in ethanol (1 liter) was treated with a 50% solution of ethyl glyoxalate in toluene (60 ml, 294 mmol) and heated to reflux for 2 hours. The mixture was left at room temperature overnight and filtered affording 5-triisopropylsilanyloxy-1H-quinoxalin-2-one. The filtrate was evaporated and the residue chromatographed eluting with a 0-3% gradient of methanol in dichloromethane affording 8-triisopropylsilanyloxy-1H-quinoxalin-2-one as a white solid (14.9 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. filtrationfiltered

Sources & evidence

ORD record
ord-8e48fa92329d47afab187f65271c260e
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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