Benzene → 5,7-Diphenylquinolin-8-ol

HRID 1436953Notes

Reaction equation

HRID 1436953 reaction equation
Br[C:2]1[CH:11]=[C:10](Br)[C:9]([O:13]C(C)C)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].CCO.[CH:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:17]1([C:2]2[CH:11]=[C:10]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:9]([OH:13])=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[N:7]3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 241BenzeneHCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 579393175,7-Dibromo-8-[(propan-2-yl)oxy]quinoline

Product 1

HCID 579393255,7-Diphenylquinolin-8-olYield 91%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Reaction of 5,7-diiodo-quinolin-8-ol with 2-bromopropane following the method described in Example 8 gave 5,7-dibromo-8-isopropoxy-quinoline 7 (93%): 1H NMR (CDCl3): δ 8.86 (dd, J=1.5 and 4.4, 1 H), 8.46 (s, 1H), 8.33 (dd, J=1.5 and 8.5, 1 H), 7.49 (dd, J=4.4 and 8.5, 1 H), 5.40 (m, 1H), 1.43 (d, J=6.1, 6 H). To a stirred mixture of 7 (200 mg, 0.51 mmol), phenylboronic acid (143 mg, 1.17 mmol), 2 N Na2CO3 (7.2 mL), EtOH (1.2 mL) and benzene (6 mL) was added, under a blanket of argon, Pd(PPh3)4 (21 mg). The mixture was stirred under reflux for 16 h, cooled and concentrated. This provided, after column chromatography on silica (ethyl acetate/hexane, 1:9), 5,7-diphenyl-8-isopropoxy-quinoline as a yellow solid (157 mg, 91%). Cleavage of the isopropoxy group following the method outlined in Example 8 gave 5,7-diphenyl-8-hydroxy-quinoline M1 in 91% yield. (See table 4 for data).

Workup

  1. temperatureunder reflux for 16 h
  2. temperaturecooled
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7e2051dc2442410689ca2b98e359226a
Source dataset
uspto-grants-2009_11
Patent number
US07619091B2

Reaction notes

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