3-Amino-1-propanol → Methyl 2-[(3-hydroxypropyl)amino]-3-nitrobenzoate
Reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH2:15][CH2:16][CH2:17][CH2:18][OH:19]>CO.C(N(CC)CC)C>[OH:19][CH2:18][CH2:17][CH2:16][NH:15][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of methyl 2-chloro-3-nitrobenzoate (100 g, 0.463 mol) in methanol (800 mL) and triethylamine (129 mL) was added 3-amino-1-propanol (52.2 g, 0.696 mol), and the mixture was stirred at 50° C. for 6 hr. The mixture was concentrated and the residue was diluted with aqueous saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layer was washed, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 50% ethyl acetate/n-hexane mixture (short column). The filtrate was concentrated in vacuo to give the title compound as a brown oil (86.6 g, 0.341 mol, 74%).
Workup
- concentrationThe mixture was concentrated
- additionthe residue was diluted with aqueous saturated ammonium chloride
- extractionextracted with ethyl acetate
- washThe combined organic layer was washed
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by flash column chromatography on silica gel eluting with a 50% ethyl acetate/n-hexane mixture (short column)
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-abdc8fc04136469ba61bd4b16fb12131
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785460B2
Reaction notes
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