Acetic Acid → HCID 20474272, compound

HRID 2295902Notes

Reaction equation

HRID 2295902 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([N:10]2[N:14]=[C:13]([CH2:15][CH3:16])[C:12]([CH3:17])=[N:11]2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](OCC)=[O:29])=[CH:23][CH:22]=1)([O-:20])=[O:19].N1CCCCC1.C(O)(=O)C>C(O)C>[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([C:27]2[C:28](=[O:29])[O:1][C:2]3[C:3]([CH:4]=2)=[CH:6][CH:7]=[C:8]([N:10]2[N:14]=[C:13]([CH2:15][CH3:16])[C:12]([CH3:17])=[N:11]2)[CH:9]=3)=[CH:25][CH:26]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 79517Ethyl 4-nitrophenylacetateHCID 12412922HCID 12412922, compound

Product 1

HCID 20474272HCID 20474272, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50.6 g (200 mmols) of the Na salt of 2-hydroxy-4-(4-ethyl-5-methyl-2H-1,2,3-triazol-2-yl)-benzaldehyde, 41.8 g (200 mmols) of ethyl 4-nitrophenylacetate and 2 ml of piperidine are refluxed in 250 ml of ethanol for 4 hours. After the mixture has been cooled, it is neutralised with glacial acetic acid, and the residue is washed with ethanol and water, and dried: 46.3 g (61.5%). Recrystallisation from toluene yields 41.4 g (55%) of 3-(4-nitrophenyl)-7-(4-ethyl-5-methyl-2H-1,2,3-triazol-2-yl)-coumarin in the form of a pale yellow crystalline powder of melting point 278°-279° C.

Workup

  1. temperatureAfter the mixture has been cooled
  2. washthe residue is washed with ethanol and water
  3. customdried
  4. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-ba219a2abac0453aaa637d8ed74a58d1
Source dataset
uspto-grants-1984_01
Patent number
US04426530

Reaction notes

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