Aniline → Phenoxazine

HRID 2363265Notes

Reaction equation

HRID 2363265 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9](C)([O-:11])[CH3:10].[Na+].[C:14](P(C(C)(C)C)C(C)(C)C)(C)([CH3:16])[CH3:15]>C1(C)C(C)=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:15]1[C:10]2[NH:1][C:2]3[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=3)[O:11][C:9]=2[CH:8]=[CH:16][CH:14]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxide

Product 1

HCID 67278Phenoxazine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
60 °C

Procedure

17 g (41 mmol) of Compound b, 7.6 g (82 mmol) of aniline, 7.4 g (77 mmol) of sodium tert-butoxide, 0.61 g (1.1 mmol) of Pd2(dba)3 [(tris(dibenzylidine acetone) dipalladium(0))], and 0.22 g (1.1 mmol) of tri(tert-butyl)phosphine were dissolved in 200 mL of xylene, and then refluxed at 60° C. for 1 hour.

Sources & evidence

ORD record
ord-2edb7e093621494e8e4dc671e60c4aad
Source dataset
uspto-grants-2014_04
Patent number
US08691930B2

Reaction notes

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