'Femme Endormie' (Sleeping Woman) was done early in Friedlaender's career and was printed "chine collé" (a thin sheet of Asian paper collaged to a heavier support sheet). It was published by the L'Oeuvre Graveé of Paris and Zurich and is one of his last figurative prints, by 1957 his work became almost completely abstract and was printed using color.
Friedlaender learned printmaking from Otto Mueller in Breslau. He and his young wife fled the Nazi regime in 1937 settling in Paris as political refugees. In 1938 and 1939, Friedlaender worked at the literary weekly magazine Marianne on Paul Chadourne's recommendation. From 1939 to 1943 he was interned in a series of concentration camps. After the war, the Friedlaenders returned to Paris in 1945, in 1947 he became a member of the Salon de Mai, and in 1950 he became a French citizen.