2-Pyrrolidone → 10-(1-Pyrrolin-2-YL)-2-(trifluoromethyl)phenoxazine

HRID 2163235Notes

Reaction equation

[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][C:20]1=O.P(Cl)(Cl)(Cl)=O>>[N:19]1[CH2:23][CH2:22][CH2:21][C:20]=1[N:6]1[C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:16]=[CH:15][C:14]=2[O:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2

Participants

Reactant 3

HCID 120252-Pyrrolidone

HCID 24813Phosphorus oxychloride

HCID 104673212-Trifluoromethylphenoxazine

Product 1

HCID 2275428010-(1-Pyrrolin-2-YL)-2-(trifluoromethyl)phenoxazine

Procedure

Reaction of 2-(trifluoromethyl)phenoxazine, 2-pyrrolidinone and phosphorus oxychloride according to the procedure of Example 1 provides the free base 10-(1-PYRROLIN-2-YL)-2-(TRIFLUOROMETHYL)PHENOXAZINE as a distallable oil, b.p. 140-146° C. at 0.1 mm Hg. Conversion of the free base to the hydrochloride salt affords 10-(1-PYRROLIN-2-YL)-2-(TRIFLUOROMETHYL)PHENOXAZINE HYDROCHLORIDE, m.p. 219.5-222.5° C. (dec.) (corr.), in a 62% overall yield by triturating with warm benzene.

Sources & evidence

ORD record: ord-1e6d7f75bae94c7fb0567e6267de4ed1
Source dataset: uspto-grants-1979_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04132794

Reaction notes

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