Ethanol → HCID 53730872, compound

HRID 1681699Notes

Reaction equation

HRID 1681699 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[C:6]([NH:8][CH2:9][C:10]#[CH:11])=[O:7])([O-])=O.[N+](C1C=CC=CC=1C(Cl)=O)([O-])=O.C(N)C#C.C(O)C>CO.O>[CH:9]([N:8]1[C:6](=[O:7])[C:5]2[C:4](=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:1]1)=[C:10]=[CH2:11]

Participants

7

Reactant 4

HCID 702EthanolHCID 118752-Nitrobenzoyl chlorideHCID 239041PropargylamineHCID 19805520HCID 19805520, compound

Product 1

HCID 53730872HCID 53730872, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Using a similar procedure to that described in Examples 2-16, but starting from 2-nitro-N-(prop-2-ynyl)benzamide (itself prepared from 2-nitrobenzoyl chloride and prop-2-ynylamine using the process described for the preparation of the starting material for Ex. 24), using a mixture of ethanol and water (95/5 v/v) in place of aqueous methanol as the reaction solvent and having a reaction duration of 3 hours, there was obtained 1,2-dihydro-2-allenyl-3H-indazol-3-one (Ex. 177) as a solid, m.p. 126-130° C. in 12% yield.

Workup

  1. customdescribed for the preparation of the starting material for Ex
  2. customa reaction duration of 3 hours

Sources & evidence

ORD record
ord-7cf3188c301f4305a5323d0961e3de6d
Source dataset
uspto-grants-1992_12
Patent number
US05173496

Reaction notes

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