2-(Dimethoxymethyl)tetrahydro-2,5-dimethoxyfuran → 9-(2-Formyl-1-pyrrolyl)benzo[f]quinoxaline-2,3(1H,4H)-dione

HRID 1457567Notes

Reaction equation

HRID 1457567 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:14]=[CH:13][C:12]3[NH:11][C:10](=[O:15])[C:9](=[O:16])[NH:8][C:7]=3[C:6]=2[CH:17]=1.CO[C:20]1([CH:27](OC)OC)[CH2:24][CH2:23][CH:22](OC)[O:21]1>C(O)(=O)C>[CH:22]([C:23]1[N:1]([C:2]2[CH:3]=[CH:4][C:5]3[CH:14]=[CH:13][C:12]4[NH:11][C:10](=[O:15])[C:9](=[O:16])[NH:8][C:7]=4[C:6]=3[CH:17]=2)[CH:27]=[CH:20][CH:24]=1)=[O:21]

Participants

4

Reactant 2

HCID 30333232-(Dimethoxymethyl)tetrahydro-2,5-dimethoxyfuranHCID 22097114HCID 22097114, compound

Product 1

HCID 221001569-(2-Formyl-1-pyrrolyl)benzo[f]quinoxaline-2,3(1H,4H)-dioneYield 27%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7.0 g (30.8 mmol) of 9-aminobenzo[f]quinoxaline-2,3(1H,4H)-dione and 6.4 g (30.8 mmol) of 2,5-dimethoxy-2-(1,1-dimethoxymethyl)tetrahydrofuran were refluxed in 170 ml of glacial acetic acid for 30 minutes. The precipitate was filtered off with suction and purified by chromatography on silica gel (mobile phase: toluene/acetone/glacial acetic acid=10/10/1). 2.5 g (27%) of the product were obtained. Melting point >250° C.

Workup

  1. filtrationThe precipitate was filtered off with suction
  2. custompurified by chromatography on silica gel (mobile phase: toluene/acetone/glacial acetic acid=10/10/1)

Sources & evidence

ORD record
ord-c33a11763f394bff9448f103bead361a
Source dataset
uspto-grants-1998_12
Patent number
US05849743

Reaction notes

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