Hydroxyacetone → 1-Propanol, 2-[(2,3,4-trifluorophenyl)amino]-
Reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][CH:7]([CH3:10])[CH2:8][O:9][C:4]=2[C:3]=1[F:13].[F:14]C1C(F)=C(F)C=CC=1N.FC1C=CC([N+]([O-])=O)=C(F)C=1F.OCC(=O)C>>[OH:9][CH2:8][CH:7]([NH:6][C:5]1[CH:11]=[CH:12][C:2]([F:1])=[C:3]([F:13])[C:4]=1[F:14])[CH3:10]Participants
5
Procedure
A method for the preparation of 7,8-difluoro-2,3-dihydro-3-methyl-4H-1,4-benzoxazine either as the optically active s-(-)-7,8-difluoro-2,3-dihydro-3-methyl-4H-1,4-benzoxazine or the racemic mixture. The process of the invention comprises the reaction of 2,3,4-trifluoroaniline or trifluoronitrobenzene with hydroxyacetone or a hydroxyacetone derivative under reducing condition to yield N-(3-hydroxy-2-propyl)-2,3,4-trifluoroaniline derivative. The N-(3-hydroxy-2-propyl)-2,3,4-trifluoroaniline is treated with base to yield the benzoxazine intermediate.
Sources & evidence
- ORD record
- ord-ef891973ea5e44ec885fdee9ab3dfaa2
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05986140
Reaction notes
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