Acetic Anhydride → N-(3-fluoro-2-methylphenyl)acetamide
Reaction equation
[F:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:10](OC(=O)C)(=[O:12])[CH3:11]>>[F:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH:5][C:10](=[O:12])[CH3:11]Participants
3
Procedure
3-Fluoro-2-methylaniline was acetylated with acetic acid anhydride to give 3-fluoro-2-methyl-N-acetylaniline. Displacing fluorine of the 3-fluoro-2-methyl-N-acetylaniline with methylamine followed by nitration, deacetylation and reduction of the nitro group with palladium or charcoal gave 1,2-diamino-3-methyl-4-methylaminobenzene. Condensation of 4,4′-dibromo-benzil with the 1,2-diamino-3-methyl-4-methylaminobenzene in refluxing methanol gave 2,3-bis(4-bromophenyl)-5-methyl-6-methylaminoquinoxaline which upon acetylation with acetic acid anhydride, nitration, reduction with palladium on charcoal and cyclization gave the title compound.
Sources & evidence
- ORD record
- ord-b1f4f0ce1afa41bfbe7838bf08df8bfc
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06656940B2
Reaction notes
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