Acridan → 9,10-Dihydro-10-phenylacridine

HRID 2188225Notes

Reaction equation

HRID 2188225 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:16]1([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13][C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 7106AcridanHCID 7961BromobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 149414419,10-Dihydro-10-phenylacridineYield 98%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

18.12 g of acridan (0.10 mol), 17.30 g of bromobenzene (0.11 mol), 14.40 g of sodium t-butoxide (0.15 mol), 1.12 g of Pd(OAc)2 (5 mmol), and 0.81 g of tri-t-butylphosphine (4 mmol) were taken up in 100 mL of dry toluene and this reaction mixture was allowed to stir under inert atmosphere. The exothermic reaction heated to reflux, then cooled to room temperature and was allowed to stir for 1 h. TLC analysis showed the reaction had gone to completion, so the reaction mixture was passed through a short plug of silica gel, which was subsequently washed with 1 L of CH2Cl2. The filtrate was concentrated to dryness and purified by column chromatography to afford 25.21 g of the N-phenylacridan (98.0%).

Workup

  1. customThe exothermic reaction
  2. temperatureheated
  3. temperatureto reflux
  4. stirringto stir for 1 h
  5. washwas subsequently washed with 1 L of CH2Cl2
  6. concentrationThe filtrate was concentrated to dryness
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-2b95a77f060849b5a5aca4c22e0a752c
Source dataset
uspto-grants-2002_06
Patent number
US06410732B2

Reaction notes

Loading…