Formic Acid → HCID 21491300, compound

HRID 1973376Notes

Reaction equation

HRID 1973376 reaction equation
[CH:1]([OH:3])=[O:2].C(OC(=O)C)(=O)C.O[CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[C:16]([C:24]([OH:26])=[O:25])[C:15]1=[O:27]>N1C=CC=CC=1>[CH:1]([O:3][CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[C:16]([C:24]([OH:26])=[O:25])[C:15]1=[O:27])=[O:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 21491295HCID 21491295, compound

Product 1

HCID 21491300HCID 21491300, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Formic acid (3 ml., 98%) was added dropwise to acetic anhydride (6 ml) which was cooled below 5°. The mixture was heated at 50° for 15 minutes and cooled to below 5° and added slowly to a cold (5°-10°) solution of 3,4-dihydro-4(2-hydroxyethyl)-3-oxo-2-quinoxalinecarboxylic acid (3.2 g) in pyridine (40 ml). The solution was allowed to warm to room temperature, stirred for 6 hours and the pyridine was distilled off under reduced pressure. Hydrochloric acid (50 ml., 2N) was added to the residue and the solid was filtered off and dried, m.p. > 100°. Attempts to recrystallise this compound from dimethylformamide resulted in the loss of the formyl group.

Workup

  1. temperaturewas cooled below 5°
  2. temperatureThe mixture was heated at 50° for 15 minutes
  3. temperaturecooled to below 5°
  4. distillationthe pyridine was distilled off under reduced pressure
  5. additionHydrochloric acid (50 ml., 2N) was added to the residue
  6. filtrationthe solid was filtered off
  7. customdried
  8. customto recrystallise this compound from dimethylformamide
  9. customresulted in the loss of the formyl group

Sources & evidence

ORD record
ord-46982a2f5fb34a39a46d1f8b920d9ae6
Source dataset
uspto-grants-1976_12
Patent number
US03997535

Reaction notes

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