4-Methoxy-2-nitrobenzonitrile → 6-Methoxy-1,2-benzoxazol-3-amine

Reaction equation

FC1C=C(OC)C=CC=1C#N.COC1C=CC(C#N)=C([N+]([O-])=O)C=1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[C:29]([O:35][N:36]=C(C)C)[CH:28]=1>>[NH2:32][C:31]1[C:30]2[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][C:29]=2[O:35][N:36]=1

Participants

Reactant 3

HCID 2886654-Methoxy-2-nitrobenzonitrile

HCID 6398782-Fluoro-4-methoxybenzonitrile

HCID 187964454-Methoxy-2-[[(1-methylethylidene)amino]oxy]benzonitrile

Product 1

HCID 106785796-Methoxy-1,2-benzoxazol-3-amine

Procedure

Alternatively, 2-Fluoro-4-methoxy-benzonitrile can be substituted for 4-methoxy-2-nitrobenzonitrile. 3-Amino-6-methoxy-1,2-benzisoxazole is prepared following substantially the procedure of Example 25a starting from 4-methoxy-2-[[(1-methylethylidene)amino]oxy]-benzonitrile.

Sources & evidence

ORD record: ord-2cd949bcfb0e41f383559d912ca0a815
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05756754

Reaction notes

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