\documentclass[12pt,border=5pt,tikz,class=scrartcl,multi=false]{standalone} \usepackage{times} \usepackage[T1]{fontenc} \usepackage[latin1]{inputenc} \usepackage{mathtools,amssymb,siunitx} \usepackage{pgfplots} \pgfplotsset{compat=1.13} \usepackage{gensymb} \usepackage{chemfig,chemmacros} \renewcommand*{\familydefault}{\sfdefault} \renewcommand*\printatom[1]{\ensuremath{\mathsf{#1} } } \setatomsep{1.5em} \setdoublesep{.6ex} \setarrowdefault{,1,ultra thick} \setbondstyle{very thick,cap=round} \definesubmol\nobond{-[,0.2,,,draw=none]} \pagestyle{empty} \thispagestyle{empty} \begin{document} \schemedebug{false} \schemestart[][west] \chemfig{ *6((-HO)-=(-N(-[0]H)-[6]ts)-=-=) } \arrow{->[*{0}\mbox{\color{blue}1]}]}[-90,,blue] \chemfig[blue]{ *6((-HO)=-(-[:-30]N(-[6]ts)-[:30]-[::60]-[::60](=[2]O)-[::50,0.7]H)=-=-) } \arrow{->}[-90,,blue] \chemfig[blue]{ *6((-HO)=- (-[:-30]N(-[6]ts)-[:30]-[::60]-[::60](-[2]O-[::-71]Et)(-[:30]O-[0]Et) -[::50,0.7]H)=-=-) } \arrow{->[\mbox{\color{red}2]}]}[,,red] \subscheme{ \chemfig[red]{ *6((-HO)=-(-[:-30]N(-[6]ts)-[:30]-[::60]-[::60](=[2]O)-[::50,0.7]H)=-=-) } \arrow{<=>}[-90,,red] \chemfig[red]{ *6((-HO)=-(-[:-30]N(-[6]ts)-[:30]-[::60]=^[::60](-[2]OH)-[::50,0.7]H)=-=-) } } \arrow{->}[,,red] \chemfig[red]{ *6((-HO)=-(*6(-N(-ts)---(-OH)-))=-=-) } \arrow{->[*{0}\mbox{\color{green}3]}]}[90,,green] \chemfig[green]{ *6((-HO)=-(*6(-N(-ts)--=-))=-=-) } \arrow{->[*{0}\mbox{\color{magenta}4]}]}[90,1.75,magenta] \chemfig{ *6((-HO)=-(*6(-N=-=-))=-=-) } \arrow(@c1.east--){->[\chemfig{ -(-[::60])-[::-60]N(-[0]H)-[::-60](-[::-60])-[::60] } / \ch{EtOH}][\parbox{6.5cm}{ {\color{blue}1] \textminus7\textdegree C, 4hrs} \chemfig[blue]{H-[:30](=[2]O)-[:-30]=_[6]}\\ {\color{red}2] 6N \ch{HCl} 20\textdegree C, 16hrs, 45\textdegree C 4hrs}\\ {\color{green}3] \ch{KOH}, reflux, 24hrs}\\ {\color{magenta}4] 5N \ch{HCl} to \pH=7, 0\textdegree C} }]}[,3.5] \chemmove{ \node at (-230pt,20pt) {I}; \node at (-300pt,-170pt) {Ia}; \node at (-300pt,-320pt) {Ib}; \node at (-35pt,-240pt) {Ic}; \node at (-35pt,-370pt) {Ic'}; \node at (40pt,-320pt) {Id}; \node at (40pt,-170pt) {Ie}; \node at (40pt,30pt) {III}; \node at (-75pt,-40pt) {II}; } \schemestop \end{document}