(2-Cyanoethyl)hydrazine → HCID 178440339, compound

HRID 1162857Notes

Reaction equation

C(O[C:4]([CH:6]([C:17](=O)[CH:18]([CH3:20])[CH3:19])[CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)=[O:5])C.[C:22]([CH2:24][CH2:25][NH:26][NH2:27])#[N:23]>C(O)(=O)C>[C:22]([CH2:24][CH2:25][N:26]1[C:4]([OH:5])=[C:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:15][CH:16]=2)[C:17]([CH:18]([CH3:19])[CH3:20])=[N:27]1)#[N:23]

Participants

Conditions

Temperature: 100 °C

Procedure

15 g of compound 45 are dissolved in 100 ml of glacial acetic acid. 7.4 ml of 2-cyanoethylhydrazine are added, and the solution is heated at 100° C. for 2 h. The mixture is added to ice-water and extracted several times with ethyl acetate. The organic phase is extracted with 20% strength ammonium chloride solution and saturated sodium chloride solution and dried over sodium sulfate. 2.40 g of the desired compound 46 crystallize out with the ethyl acetate phase. The mother liquor is concentrated and chromatographed on silica gel (dichloromethane:methanol:glacial acetic acid=100:10:1). A further 1.10 g of compound 46, plus 7.0 g of reisolated precursor 45, are obtained. C17H19N3O3 (313.4); MS (ESI+): 314.2 (M+H)+, tR=0.97 min (Gradient 2).

Workup

extractionextracted several times with ethyl acetate
extractionThe organic phase is extracted with 20% strength ammonium chloride solution and saturated sodium chloride solution
dry with materialdried over sodium sulfate
custom2.40 g of the desired compound 46 crystallize out with the ethyl acetate phase
concentrationThe mother liquor is concentrated
customchromatographed on silica gel (dichloromethane:methanol:glacial acetic acid=100:10:1)

Sources & evidence

ORD record: ord-7edfa9b368dd42f88b58a8ca6cf09f85
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820804B2

Reaction notes

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