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2‐Hydroxycinchoninic acid reactant: 600 g. (4.1 moles) of isatin intermediate: N‐acetylisatin product: 2‐Hydroxycinchoninic acid

In the synthesis of j3-dialkylaminoethyl-l-naphthalenemethanols, I, CH(OH)CX2CH2NR2 Z\Z\ VU Y I the failure of the method involving preparation and reduction of the Mannich ketones (1) in those cases where Y = Cl, X = H or Y = CH30, X = CH3 led to the investigation of other methods. The synthesis of compounds representative of this second case (Y = CH30, X = CH3) was accomplished successfully by treatment of a,a-dimethyl-/3dialkylaminopropionaldehyde with 4-methoxy-l-naphthylmagnesium bromide: MgBr zX/\ + R2NCH2C(CH3)2CHO och3 CH( OH) C (CH3)2 CH2NR2 z\A och3The a ,a-dimethyl-/3-dialkylaminopropionaldehydes were readily prepared according to the method of Mannich, Lesser, and Silten (2). The preparation of several of these compounds has been recorded in the literature: methylamino (3), dimethylamino (2), diethylamino (2), piperidino (2), and morpholino (4). We have extended the series to include those amino aldehydes containing the di-npropyl, di-n-butyl, and di-n-amyl groupings. The properties of these compounds are summarized in Table I.The Grignard reagent prepared from l-bromo-4-methoxynaphthalene (5) re-

Angeles. The survey number, designated SN, identifies a drug in the records of the Survey of Antimalarial Drugs. The antimalarial activity of those compounds to which such numbers have been assigned will be tabulated in a forthcoming monograph.