3-Methyl-6-nitro-1H-indazole → 1-(2-Carboxy-3-methoxyphenyl)-3-methyl-6-nitroindazole
Reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.Br[C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:16]=1[C:17]([OH:19])=[O:18]>>[C:17]([C:16]1[C:20]([O:24][CH3:25])=[CH:21][CH:22]=[CH:23][C:15]=1[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[C:2]([CH3:1])=[N:3]1)([OH:19])=[O:18]Participants
3
Procedure
3-Methyl-6-nitroindazole (5.31 g) and 6.93 g of 2-bromo-6-methoxybenzoic acid were subjected to reaction in the same manner as in Example 11 to obtain 1-(2-carboxy-3-methoxyphenyl)-3-methyl-6-nitroindazole (yield: 75.9%). The nitro group of the compound was reduced to give 6-amino-(2-carboxy-3-methoxyphenyl)-3-methylindazole (yield: 100%), which was then cyclized to obtain 1.83 g (28.9%) of 5-amino-7-methoxy-2-methyl-6H-pyrazolo[4,5,1-d,e]acridin-6-one.
Sources & evidence
- ORD record
- ord-0aee6d717ed649999a5d47c14b1409c4
- Source dataset
- uspto-grants-1992_01
- Patent number
- US05079358
Reaction notes
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