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Formic Acid → HCID 13175327, compound

HRID 2418217
Notes
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Reaction equation

HRID 2418217 reaction equation
[CH:1](O)=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[O:16]=[C:17]1[N:22]2[C:23]3[C:28]([NH:29][CH2:30][C:21]2=[N:20][CH:19]=[C:18]1[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:27][CH:26]=[CH:25][CH:24]=3.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:1]([N:29]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]2[C:17](=[O:16])[C:18]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:19][N:20]=[C:21]2[CH2:30]1)=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 284Formic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 13175315HCID 13175315, compound

Product 1

HCID 13175327HCID 13175327, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A solution of 700 mg of formic acid (98%) in 70 ml of CH2Cl2 was stirred at room temperature under nitrogen while 100 mg of carbonyldiimidazole were added thereto. After 30, minutes 1.5 g of ethyl 5,6-dihydro-1-oxo-1H-pyrimido [1,2-a] quinoxaline-2-carboxylate were added thereto and the mixture was stirred for another 6 hours. Then, the solution was poured into an aqueous NaHCO3 solution and extracted with ethyl acetate. The organic layer was dried over MgSO4, decolorized with charcoal and evaporated to dryness. The residue was crystallized from ethyl acetate to obtain 1.1 g (67% yield) of ethyl 5,6-dihydro-6-formyl-1-oxo-1H-pyrimido [1,2-a] quinoxaline-2-carboxylate melting at 172°-4° C.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated to dryness
  5. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-32914cbb66e049fcb1ff7cb2221fb5c5
Source dataset
uspto-grants-1984_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04472401

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes