Triethylamine → HCID 178460078, compound

HRID 2398766Notes

Reaction equation

HRID 2398766 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([NH:17][C:18](=[O:21])[CH2:19][CH3:20])[CH:11]=1.[C:22]([C:25]1[C:26](=[O:36])[O:27][C:28]([OH:35])=[C:29]([C:32](=O)[CH3:33])[C:30]=1[OH:31])(=[O:24])[CH3:23]>CO>[C:22]([C:25]1[C:26](=[O:36])[O:27][C:28](=[O:35])[C:29](=[C:32]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([NH:17][C:18](=[O:21])[CH2:19][CH3:20])[CH:11]=2)[CH3:33])[C:30]=1[OH:31])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21434075HCID 21434075, compoundHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 178460078HCID 178460078, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Following the procedures of Example 3, 2.0 g. (0.0096 mol) of 4-nitro-2-propionamidophenyl (prepared from propionic acid and 2-amino-4-nitrophenyl) is hydrogenated in a mixture of 100 ml. of ethanol, 0.3 g. of 10% palladium-on-carbon and 1.34 ml. of concentrated hydrochloric acid in a Parr apparatus. Filtration and evaporation of the solvent gives 4-amino-2-propionamidophenol hydrochloride. The latter (2.0 g., 0.0096 mol) in a methanol solution is treated with 1 equivalent of triethylamine under nitrogen atmosphere. The solution of the free amine is added to a refluxing mixture of one equivalent of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one and 30 ml. of methanol under nitrogen. The reaction mixture is refluxed for 18 hours, filtered and the solid is recrystallized from ethanol to yield 5-acetyl-4-hydroxy-3-[1-(4-hydroxy-3-propionamidophenylamino)ethylidene]-2H-pyran-2,6(3H)-dione, m.p. 228°-229° C. (dec.).

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hours
  2. filtrationfiltered
  3. customthe solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-dbfb5a029294417c81f6dfaa3cf75357
Source dataset
uspto-grants-1977_05
Patent number
US04025642

Reaction notes

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