Hydrochloric Acid → HCID 53693229, compound

HRID 544166Notes

Reaction equation

HRID 544166 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]2[O:14][C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][C:17](=[O:19])[CH:18]=2)=[CH:7][CH:6]=1)([O-])=O>C(O)C.O.[Fe]>[NH2:2][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]2[O:14][C:15]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:16][C:17](=[O:19])[CH:18]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 313Hydrochloric Acid2×HCID 53949379HCID 53949379, compound

Product 1

HCID 53693229HCID 53693229, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of concentrated hydrochloric acid (0.2 ml) in ethanol (20 ml) was added to a stirred refluxing suspension of 2-[2-(4-nitrophenyl)-ethenyl]-6-phenyl-4H-pyran-4-one (8.5 g) and iron powder (4.5 g) in ethanol (80 ml) and water (20 ml). The stirred mixture was heated under reflux for 5 hours, adding further concentrated hydrochloric acid (0.2 ml) after 2 hours. The hot mixture was filtered and the filtrate was evaporated under vacuum. The solid residue was crystallised from chloroform-petroleum ether 60°-80° C. to give 2-[2-(4-aminophenyl)ethenyl]-6-phenyl-4H-pyran-4-one (mp 192°-194° C.).

Workup

  1. temperaturerefluxing
  2. temperatureThe stirred mixture was heated
  3. temperatureunder reflux for 5 hours
  4. filtrationThe hot mixture was filtered
  5. customthe filtrate was evaporated under vacuum
  6. customThe solid residue was crystallised from chloroform-petroleum ether 60°-80° C.

Sources & evidence

ORD record
ord-61469cb986ca4a82bef48893776293f4
Source dataset
uspto-grants-1984_05
Patent number
US04448787

Reaction notes

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