Formic Acid → N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide
Reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.Cl.[NH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=1>O1CCCC1>[OH:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][NH:12][CH:1]=[O:2])=[CH:16][C:17]=1[O:22][CH3:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Formic acid (230 g, 5.0 mol) is added dropwise to acetic anhydride (383 g, 3.75 mol) at 0° C. This mixture is stirred for 2 hours at +55° C. and subsequently cooled again to 0° C. Tetrahydrofuran (500 ml) is added at this temperature followed by 4-(2-amino-ethyl)-2-methoxyphenol hydrochloride (50 g, 0.25 mol). The resulting white suspension is stirred for 18 hours at +75° C., changing into a yellow solution. The reaction mixture is evaporated and the residue is submitted to flash-chromatography to yield N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-formamide.
Workup
- stirringThe resulting white suspension is stirred for 18 hours at +75° C.
- customThe reaction mixture is evaporated
Sources & evidence
- ORD record
- ord-c5b198bb6b904bea99200b2f7d29f02c
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700522B2
Reaction notes
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