Ethanol → HCID 54188817, compound

HRID 1085972Notes

Reaction equation

HRID 1085972 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([NH:16][NH2:17])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].[C:18]([C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)(=O)[CH3:19].C(O)C>C(O)(=O)C.O1CCCC1>[N:24]1[CH:25]=[CH:26][C:21]([C:18](=[N:17][NH:16][C:14]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:15])[CH3:19])=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 142824-AcetylpyridineHCID 15133115HCID 15133115, compound

Product 1

HCID 54188817HCID 54188817, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.0 gm of (0.0216 mole) of 3-nitro-1-naphthalenecarboxylic acid hydrazide, 2.62 gm (0.0216 mole) of 4-acetylpyridine, 400 ml of ethanol, 100 ml of tetrahydrofuran, and 20 drops of glacial acetic acid was refluxed 10 hr. The hot solution was filtered. The filtrate was cooled to room temperature and then chilled. The product was collected, washed with Skellysolve B and dried to furnish 6.31 gm (87%) of the title compound having a melting point of 228.5° C.

Workup

  1. temperaturewas refluxed 10 hr
  2. filtrationThe hot solution was filtered
  3. temperaturechilled
  4. customThe product was collected
  5. washwashed with Skellysolve B
  6. customdried

Sources & evidence

ORD record
ord-e73d19421e4e445897a59b972b2988e7
Source dataset
uspto-grants-1991_04
Patent number
US05011932

Reaction notes

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