Formic Acid → HCID 20450293, compound

HRID 358027Notes

Reaction equation

HRID 358027 reaction equation
[CH:1](O)=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:16]1[N:20]2[C:21]3[C:26]([NH:27][CH2:28][C:19]2=[N:18][C:17]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:25][CH:24]=[CH:23][CH:22]=3.CCOCC>ClCCl>[CH:1]([CH:28]1[NH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]2[CH:16]=[C:17]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:18]=[C:19]12)=[O:2]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 3283Diethyl EtherHCID 682631,1'-CarbonyldiimidazoleHCID 13228326Ethyl 4,5-dihydroimidazo[1,2-a]quinoxaline-2-carboxylate

Product 1

HCID 20450293HCID 20450293, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.70 g of 98% formic acid in 70 ml of dichloromethane was stirred under dry nitrogen with 2.5 g of carbonyldiimidazole for 15 minutes and 1.4 g of ethyl 4,5-dihydroimidazo[1,2-a]quinoxaline-2-carboxylate were added. The mixture was stirred at room temperature for 6 hours under nitrogen and was then poured into ice/aqueous bicarbonate and filtered. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to a low volume. Dilution with ether gave 1.1 g (70% yield) of ethyl 4-formyl-4,5-dihydroimidazo[1,2-a]quinoxaline-2-carboxylate as colorless crystals after crystallization from dichloromethane/diethyl ether.

Workup

  1. additionwas then poured into ice/aqueous bicarbonate
  2. filtrationfiltered
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated under reduced pressure to a low volume

Sources & evidence

ORD record
ord-899b2bd21f014a488b054e1284dd72f8
Source dataset
uspto-grants-1984_08
Patent number
US04464373

Reaction notes

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