1,2-Cyclohexanedione → HCID 58409399, compound

HRID 386977Notes

Reaction equation

HRID 386977 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=O.[C:9]1([C:15]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]=2[NH2:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[C:22]1([C:18]2[CH:19]=[CH:20][CH:21]=[C:15]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:16]=2[NH:17][C:2]2[C:1](=[O:8])[CH2:6][CH2:5][CH2:4][CH:3]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 130061,2-CyclohexanedioneHCID 110102262,6-diphenylaniline

Product 1

HCID 58409399HCID 58409399, compoundYield 116.7%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

Follow a procedure similar to that of Preparation 2 except use 1,2-cyclohexanedione (1.0099 g, 9.0065 mmol); 2,6-diphenylaniline (2.2258 g, 9.0731 mmol); toluene (22 mL); p-toluenesulfonic acid monohydrate (0.0859 g, 0.4516 mmol); reflux reaction mixture for 2.3 hours; to isolate 3.5678 g of a brown thick oil. Purify the thick oil be chromatography using a Biotage SNAP 50 g KP-Sil column, loading the thick oil with small amount of 4% ethyl acetate/96% hexanes and 100% ethyl acetate and eluting with a gradient of 4-8% ethyl acetate in hexanes to afford after isolation 1.1388 g (37.2%) of the 2-((1,1′:3′,1″-terphenyl)-2′-ylamino)-2-cyclohexen-1-one as a yellow thick oil.

Workup

  1. customof Preparation 2
  2. temperaturereflux
  3. customreaction mixture for 2.3 hours

Sources & evidence

ORD record
ord-b9de8a31f5ed4747b4f7cd59ea30759d
Source dataset
uspto-grants-2013_02
Patent number
US08372927B2

Reaction notes

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