2H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro-1-methyl- → 1-(2-Methylamino-5-chlorobenzoyl)-1H-indazol-3-ol

HRID 485750Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([OH:10])=[N:2]1.[CH3:11][N:12]1C(=O)O[C:15](=[O:16])[C:14]2=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=[C:13]12>>[CH3:11][NH:12][C:13]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:14]=1[C:15]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([OH:10])=[N:2]1)=[O:16]

Participants

Reactant 2

HCID 267242H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro-1-methyl-

HCID 81829Indazolinone

Product 1

HCID 1784821481-(2-Methylamino-5-chlorobenzoyl)-1H-indazol-3-olYield 33.5%

Procedure

1H-Indazol-3-ol was reacted with N-methyl-5-chloroisatoic anhydride according to the general procedure A above and afforded the desired amine as a yellow solid in 33.5% yield; m.p. 210°-213° C.

Sources & evidence

ORD record: ord-8fe2ed2019f7483aa6fa2ac88f9e5b10
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04537966

Reaction notes

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