4-Methylmorpholine → N'-(3,3-dimethylbutanoyl)-4-nitrobenzohydrazide

HRID 717986Notes

Reaction equation

HRID 717986 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([NH:10][NH2:11])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].CN1CCOCC1.[CH3:21][C:22]([CH3:28])([CH3:27])[CH2:23][C:24](Cl)=[O:25]>ClCCl>[CH3:21][C:22]([CH3:28])([CH3:27])[CH2:23][C:24]([NH:11][NH:10][C:8](=[O:9])[C:7]1[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:25]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 815143,3-Dimethylbutanoyl chlorideHCID 3693744Benzoic acid, 4-nitro-, hydrazide

Product 1

HCID 4628581N'-(3,3-dimethylbutanoyl)-4-nitrobenzohydrazide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-nitrobenzohydrazide (0.500 g, 2.76 mmol), and 4-methylmorpholine (0.455 ml, 4.14 mmol) were stirred in dichloromethane (20 ml). 3,3-Dimethylbutanoyl chloride (0.422 ml, 3.04 mmol) was added and the reaction mixture was stirred for 2 hours. Normal phase chromatography of the crude reaction mixture gave the title compound.

Workup

  1. customNormal phase chromatography of the crude reaction mixture

Sources & evidence

ORD record
ord-9e83f9fe4bf64f14b526e16b525b28eb
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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