Hydrazine hydrate (1:1) → Ethyl 7-chloro-5-methyl-4-oxo-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate

HRID 2214458Notes

Reaction equation

HRID 2214458 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:17](=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:7]([C:12](OCC)=[O:13])[N:8]2[CH3:11])=[CH:4][CH:3]=1.O.[NH2:25][NH2:26]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:26][NH:25][C:12](=[O:13])[C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15461899Ethyl 6-chloro-2-(ethoxycarbonyl)-1-methyl-oxo-1h-indole-3-acetate

Product 1

HCID 21948013Ethyl 7-chloro-5-methyl-4-oxo-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4.38 g (13.5 mmol) of ethyl 6-chloro-2-(ethoxycarbonyl)-1-methyl-α-oxo-1H-indole-3-acetate (disclosed in WO-A-00/44751), of 65 ml of glacial acetic acid and of 2.7 ml (55.7 mmol) of hydrazine monohydrate is brought to reflux for 3 h.

Workup

  1. temperatureto reflux for 3 h.

Sources & evidence

ORD record
ord-0a49874a73344aa7b1b5f010641fac3e
Source dataset
uspto-grants-2006_09
Patent number
US07109194B2

Reaction notes

Loading…