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Volumn , Issue 11, 2008, Pages 1729-1733

Enhanced nucleophilicity of N-aryl amides with peri-CH and their condensations with formaldehyde

Author keywords

Alcohols; Aldehydes; Amides; Condensation; Nucleophilic addition

Indexed keywords

AMIDE; FORMALDEHYDE; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CONJUGATION; POLYMERIZATION;

EID: 48549100964 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078485 Document Type: Article

Times cited : (2)

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14
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- Typical Experimental Procedure for Hydroxy-methylation of N-Aryl Amides A mixture of amides (0.54 mmol, 1 equiv, polyformaldehyde (5.40 mmol, 10 equiv, K2CO3 (0.54 mmol, 1 equiv, and PTC (TBAB, 0.02 mmol, 0.05 equiv) in dry CHCl3 was stirred for the indicated time (Table 1) at r.t. After completion of the reaction, the unreacted polyformaldehyde was removed by filtration and CHCl3 was removed under vacuum to obtain the crude products. The crude products were purified by preparative TLC on SiO2 or analyzed by 1H NMR to determine the yields. Spectroscopic Data for Products (Table 1) N- Hydroxymethyl-N-(naphthalen-1-yl)acetamide (1b) White syrup, EtOAc-CH2Cl2 (1:8) as eluant, 93% yield. 1H NMR (500 MHz, CDCl3, δ, 7.965-7.891 (m, 3 H, 7.613-7.549 (m, 2 H, 7.505 (t, J, 7.5 Hz, 1 H, 7.446 dd, J1, 7.5 Hz
- 3

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