Formic Acid → N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide

HRID 2213171Notes

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

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-methoxy-phenol 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. 1H-NMR (300 MHz, CDCl3, δ(ppm)): 2.85 (t, 2H, CH2CH2), 3.57 (t, 2H, CH2CH2), 3.82 (s, 3H, OCH3), 5.69 (bs, 1H, NH), 6.67–7.09 (m, 3H, CH arom.), 8.12 (s, 1H, CHO).

Workup

stirringThe resulting white suspension is stirred for 18 hours at +75° C.
customThe reaction mixture is evaporated

Sources & evidence

ORD record: ord-c963745c300b48fa94f121d885dfe89a
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105545B2

Reaction notes

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