Biphenyl → HCID 22646530, compound

HRID 393584Notes

Reaction equation

HRID 393584 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([NH:7][CH:8]=[C:9]2[C:14](=[O:15])OC(C)(C)OC2=O)=[CH:5][C:4]=1[O:21][CH2:22][CH2:23][O:24][CH3:25])#[N:2].C1(C2C=CC=CC=2)C=CC=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[C:1]([C:3]1[CH:20]=[C:19]2[C:6](=[CH:5][C:4]=1[O:21][CH2:22][CH2:23][O:24][CH3:25])[NH:7][CH:8]=[CH:9][C:14]2=[O:15])#[N:2]

Participants

5

Reactant 3

HCID 7095BiphenylHCID 7583Diphenyl EtherHCID 226466155-((4-Cyano-3-(2-methoxyethoxy)anilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 22646530HCID 22646530, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

5-((4-Cyano-3-(2-methoxyethoxy)anilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (840 mg, 2.4 mmol) was added in portions to a mixture of biphenyl (8 ml) and phenyl ether (22 ml) at 250° C. and the mixture stirred at that temperature for 30 minutes. The mixture was allowed to cool, hexane was added and the solid product collected by filtration and recrystallised from methylene chloride/methanol/hexane to give 6-cyano-7-(2-methoxyethoxy)-1,4-dihydroquinolin-4-one (230 mg, 38%).

Workup

  1. temperatureto cool
  2. filtrationthe solid product collected by filtration
  3. customrecrystallised from methylene chloride/methanol/hexane

Sources & evidence

ORD record
ord-825969fb9341408186ea79e9f525b8d0
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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