10-phenyl-1H-indeno[1,2-b]quinolin-11-one → 10,11-diphenyl-11H-indeno[1,2-b]quinolin-11-ol

HRID 713584Notes

Reaction equation

HRID 713584 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]3[C:25]4[CH:26]=[CH:27][CH2:28][CH2:29][C:30]=4[C:31](=[O:32])[C:16]=23)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1>[C:9]1([C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]3[C:25]4[C:30]([C:31]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)([OH:32])[C:16]=23)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 13173405410-phenyl-1H-indeno[1,2-b]quinolin-11-oneHCID 178418255HCID 178418255, compound

Product 1

HCID 11760624810,11-diphenyl-11H-indeno[1,2-b]quinolin-11-olYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dripping 1M phenylmagnesium bromide (20 ml, 20.0 mmol) into the starting material 10-phenyl-1H-indeno[1,2-b]quinolin-11-one (3.07 g, 10.0 mmol) which is dissolved in pure tetrahydrofuran, the mixed solution undergoes reaction for 24 hours at room temperature. Then, the reaction is terminated by adding ammonium chloride solution therein. Finally, 3.47 g of 10,11-diphenyl-11H-indeno[1,2-b]quinolin-11-ol is obtained by filtering the mixed solution to remove precipitates. The percentage yield is 90.0%. 10-diphenyl-11H-indeno[1,2-b]quinolin-11-ol obtained here can be also used as starting materials to produce other 6H-indeno[2,1-b]quinoline derivatives.

Workup

  1. customreaction for 24 hours at room temperature
  2. customThen, the reaction is terminated
  3. additionby adding ammonium chloride solution

Sources & evidence

ORD record
ord-594abf8213c144a6941230de9c1dd7e9
Source dataset
uspto-grants-2015_11
Patent number
US09184396B2

Reaction notes

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