Methanol → Methyl 3-amino-3-(3-nitrophenyl)propanoate

HRID 1198198Notes

Reaction equation

S(Cl)(Cl)=O.[NH2:5][CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)[CH2:7][C:8]([OH:10])=[O:9].[CH3:20]O>>[NH2:5][CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)[CH2:7][C:8]([O:10][CH3:20])=[O:9]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 2373203-Amino-3-(3-nitrophenyl)propanoic acid

Product 1

HCID 2769472Methyl 3-amino-3-(3-nitrophenyl)propanoate

Conditions

Temperature: -20 °C

Procedure

Thionyl chloride (1.11 ml) and 3-amino-3-(3-nitrophenyl)propionic acid (0.7 g) were added in turn to stirred methanol (5 ml) which had been cooled -20° C. The mixture was stirred at -20° C. for 10 minutes and at laboratory temperature for 16 hours. The mixture was evaporated to give methyl 3-amino-3-(3-nitrophenyl)propionate (0.83 g), as a solid.

Workup

customThe mixture was evaporated

Sources & evidence

ORD record: ord-a09a50b799004a7d89fa4803eaeabdc1
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05280027

Reaction notes

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