Hydrazine hydrate (1:1) → 7-chloro-3-(2,4-dimethoxyphenyl)-1H-indazole

HRID 735431Notes

Reaction equation

HRID 735431 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1F)=O.O.[NH2:22][NH2:23]>CN(C1C=CN=CC=1)C>[Cl:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]2[C:14]=1[NH:23][N:22]=[C:11]2[C:4]1[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 64713965(3-Chloro-2-fluorophenyl)(2,4-dimethoxyphenyl)methanone

Product 1

HCID 1784891417-chloro-3-(2,4-dimethoxyphenyl)-1H-indazoleYield 52.2%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Prepared as in Example 104 from (2,4-dimethoxyphenyl)[2-fluoro-3-chlorophenyl]methanone (1.20 g, 4.1 mmol), hydrazine hydrate (1.61 mL, 51.7 mmol) and DMAP (0.632 g, 5.17 mmol) to give the product (0.618 g) as a yellow solid.

Sources & evidence

ORD record
ord-7ee351c404a1498892be975dc50bafd1
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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