Hydrochloric Acid → 10-(4-Butylphenyl)-10H-phenoxazine

HRID 1014750Notes

Reaction equation

HRID 1014750 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH:23]1[C:36]2[NH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[O:28][C:27]=2[CH:26]=[CH:25][CH:24]=1.Br[C:38]1[CH:43]=[CH:42][C:41]([CH2:44][CH2:45][CH2:46][CH3:47])=[CH:40][CH:39]=1.CC(C)([O-])C.[Na+].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH2:44]([C:41]1[CH:42]=[CH:43][C:38]([N:35]2[C:36]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=3[O:28][C:29]3[C:34]2=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:39][CH:40]=1)[CH2:45][CH2:46][CH3:47]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 67278PhenoxazineHCID 80271Tri-o-tolylphosphineHCID 5210591-Bromo-4-butylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 2238164910-(4-Butylphenyl)-10H-phenoxazine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Procedure

Palladium acetate, tri-o-tolylphosphine and toluene were charged in a three-necked round-bottomed flask, and stirred for 20 minutes at room temperature. Phenoxazine, 1-bromo-4-butylbenzene, sodium t-butoxide and toluene were added, and the mixture was heated in an oil bath and refluxed for 15 hours. After cooling, concentrated hydrochloric acid was added and the mixture was stirred for 1 hour, then, the solution was passed through a neutral alumina column. The column was washed with toluene, and the solvent was removed using a rotary evaporator, to obtain yellow solid. The solid was re-crystallized from toluene/methanol, to obtain N-(4-n-butylphenyl)phenoxazine.

Workup

  1. temperaturethe mixture was heated in an oil bath
  2. temperaturerefluxed for 15 hours
  3. temperatureAfter cooling
  4. stirringthe mixture was stirred for 1 hour
  5. washThe column was washed with toluene
  6. customthe solvent was removed
  7. customa rotary evaporator
  8. customto obtain yellow solid
  9. customThe solid was re-crystallized from toluene/methanol

Sources & evidence

ORD record
ord-cd450df1776c4e0ebeef1ab83e9add8b
Source dataset
uspto-grants-2011_07
Patent number
US07982212B2

Reaction notes

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