Toluene → HCID 58897780, compound

HRID 2357860Notes

Reaction equation

HRID 2357860 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH:12]([CH3:20])[CH:13]2OC.[C:21](O[K])([CH3:24])([CH3:23])[CH3:22].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[C:40]1(C)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:22][C:21]1[CH2:24][C:3]2[C:4]([CH:23]=1)=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]([C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][C:12]([CH3:20])=[CH:13]2)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 5

HCID 1140Toluene2×HCID 6115AnilineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 64228144-Bromo-2-methyl-1-(methyloxy)-2,3-dihydro-1H-indeneHCID 178418922HCID 178418922, compound

Product 1

HCID 58897780HCID 58897780, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere, a mixture of 2.79 g (30 mmol) of aniline, 14.5 g (60 mmol) of 4-bromo-1-methoxy-2-methylindane, 20.2 g (180 mmol) of tBuOK, 30 ml of 0.2 M (6.0 mmol) solution of PtBu3 in toluene, and 180 ml toluene, 0.67 g (3.0 mmol) of Pd(OAc)2 was added. This mixture was stirred for 8 hours at 100° C. Then, this mixture was washed with 600 ml of water, and organic layer was separated. The aqueous layer was extracted with 3×150 ml of methyl-tert-butyl ether. To the combined extract, 250 ml of methanol and 150 ml of 10 M HCl were added; and the resulting mixture was refluxed for 7 hours. Sodium bicarbonate (ca. 130 g) was added in small portions until carbon dioxide evolved. The product, N,N-bis(2-methyl-1H-inden-7-yl)-N-phenylamine, was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 50 mm, l 400 mm, eluant:hexanes-dichloromethane=1:1, vol.) Yield, 7.84 g (80%) of a yellowish oil.

Workup

  1. additionwas added
  2. washThen, this mixture was washed with 600 ml of water, and organic layer
  3. customwas separated
  4. extractionThe aqueous layer was extracted with 3×150 ml of methyl-tert-butyl ether
  5. extractionTo the combined extract
  6. addition250 ml of methanol and 150 ml of 10 M HCl were added
  7. temperatureand the resulting mixture was refluxed for 7 hours
  8. additionSodium bicarbonate (ca. 130 g) was added in small portions until carbon dioxide

Sources & evidence

ORD record
ord-a6de6130cdb4435682cb0d8c647fc8bb
Source dataset
uspto-grants-2010_07
Patent number
US07763562B2

Reaction notes

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