Ammonia → N-Methyl-4-anisidine
Reaction equation
C[C:2]1OC(=O)[C:5]2[CH:11]=[C:10]([N+]([O-])=O)[CH:9]=[CH:8][C:6]=2[N:7]=1.N1C2C(=CC=CC=2)[C:19](=[O:26])NC=1.CC1NC(=O)C2C(=CC=C([N+]([O-])=O)C=2)N=1.N.ClC1C2C(=CC=CC=2)N=CN=1.[Cl:54][C:55]1[C:64]2[C:59](=[CH:60][CH:61]=[C:62]([N+:65]([O-:67])=[O:66])[CH:63]=2)[N:58]=[C:57]([CH3:68])[N:56]=1.P(Cl)(Cl)(Cl)=O>O1CCOCC1>[Cl:54][C:55]1[C:64]2[C:59](=[CH:60][CH:61]=[C:62]([N+:65]([O-:67])=[O:66])[CH:63]=2)[N:58]=[C:57]([CH3:68])[N:56]=1.[CH3:2][NH:7][C:6]1[CH:5]=[CH:11][C:10]([O:26][CH3:19])=[CH:9][CH:8]=1Participants
Reactant 7
Product 2
Reagents, catalysts & solvents 1
Procedure
Compounds of this invention with Formulae I-II, wherein R2 is an alkyl group, could be prepared as illustrated by the exemplary reaction in Scheme 9. Reaction of a substituted 2-amino-benzoic acid, such as 2-amino-5-nitro-benzoic acid, with acetic anhydride, produces the corresponding substituted 2-methyl-4H-benzo[d][1,3]oxazine-4-one, such as 2-methyl-6-nitro-4H-benzo[d][1,3]oxazine-4-one, which is converted to the corresponding quinazoline-4(3H)-one, such as 2-methyl-6-nitro-quinazoline-4(3H)-one, by treatment with ammonia in dioxane. The compound is then converted to the corresponding 4-chloro-quinazoline, such as 4-chloro-2-methyl-6-nitro-quinazoline by reaction with phosphorylchloride. Reaction of the 4-chloro-quinazoline, such as 4-chloro-2-methyl-6-nitro-quinazoline with a substituted arylamine or heteroarylamine, such as N-methyl-4-methoxy-aniline, produces the corresponding 4-(arylamino or heteroarylamino)-quinazoline, such as substituted 2-methyl-6-nitro-4-anilino-quinazoline. Other substituted 2-amino-benzoic acid that can be used for the reaction include 2-amino-4-nitro-benzoic acid, 2-amino-5-chloro-benzoic acid.
Sources & evidence
- ORD record
- ord-4afd7d7638974678b75e41b5f6a78551
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989462B2
Reaction notes
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