Ethanol → HCID 13851041, compound

HRID 986760Notes

Reaction equation

HRID 986760 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[CH:16]=[CH:15][C:14]([C:17]4([CH3:20])[O:19][CH2:18]4)=[CH:13][C:10]=3[C:11](=[O:12])[C:5]2=[CH:4][C:3]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(O)C>[C].[Pd].O1CCCC1>[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[CH:16]=[CH:15][C:14]([CH:17]([CH3:20])[CH2:18][OH:19])=[CH:13][C:10]=3[C:11](=[O:12])[C:5]2=[CH:4][C:3]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 2

HCID 702EthanolHCID 13851040HCID 13851040, compound

Product 1

HCID 13851041HCID 13851041, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 2-amino-7-(1,2-epoxy-1-methylethyl)-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate (800 mg), 5% palladium-carbon (700 mg), ethanol (50 ml) and tetrahydrofuran (150 ml) was subjected to catalytic reduction for two hours at room temperature under ordinary pressure. Then, the catalyst was filtered off, and the filtrate was concentrated to dryness. The concentrate was purified by means of a silica-gel (80 g) column chromatography using chloroform-acetone-formic acid (9:1:0.1). The solvent was evaporated off, and the residue was recrystallized from chloroform to yield colorless prisms (499 mg) of ethyl 2-amino-7-(2hydroxy-1-methylethyl)-5-oxo-5H-[1]benzopyrano[2,3-b]-pyridine-3-carboxylate, m.p. 255°-256° C.

Workup

  1. filtrationThen, the catalyst was filtered off
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe concentrate was purified by means of a silica-gel (80 g) column chromatography
  4. customThe solvent was evaporated off
  5. customthe residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-1db96eb604914114a0a5861d178f8367
Source dataset
uspto-grants-1987_12
Patent number
US04716167

Reaction notes

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