Glycine → Methyl [1-(3-propylphenyl)hydrazino]acetate

HRID 1493610Notes

Reaction equation

[NH2:1]CC(O)=O.[CH3:6][O:7][C:8](=[O:20])[CH2:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH3:19])[CH:12]=1.N([O-])=O.[Na+]>C(O)(=O)C.O.[Zn]>[CH2:17]([C:13]1[CH:12]=[C:11]([N:10]([CH2:9][C:8]([O:7][CH3:6])=[O:20])[NH2:1])[CH:16]=[CH:15][CH:14]=1)[CH2:18][CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

Glycine (Intermediate 32, 10 g, 48 mmol) was dissolved in acetic acid (50 ml) and water (5 ml). The solution was cooled to 0° C. and sodium nitrite (3.67 g, 53 mmol) in water (10 ml) was added such that the temperature did not rise above 5° C. The yellow solution turned red then brown, and was stirred at 0° C. for 1 h. The mixture was cooled to -5° C. and zinc powder (12.6 g, 193 mmol) was added very slowly such that the temperature did not rise above 0° C. The mixture was stirred at 0° C. for 5 h then poured into water (400 ml) and extracted with ethyl acetate (3×150 ml). The combined, dried (Na2SO4) organic extracts were concentrated in vacuo to give a dark yellow oil. The crude material was purified by chromatography on silica (500 g) eluted with chloroform-ethanol 98:2 to give the title compound (Intermediate 33, 1.4 g, 13%) as a yellow oil.

Workup

customdid not rise above 5° C
temperatureThe mixture was cooled to -5° C.
customdid not rise above 0° C
stirringThe mixture was stirred at 0° C. for 5 h
extractionextracted with ethyl acetate (3×150 ml)
dry with materialdried (Na2SO4) organic extracts
concentrationwere concentrated in vacuo
customto give a dark yellow oil
customThe crude material was purified by chromatography on silica (500 g)
washeluted with chloroform-ethanol 98:2

Sources & evidence

ORD record: ord-6fa64d8aef924077904fb81149ef8df8
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05023255

Reaction notes

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