Aniline → HCID 178469510, compound

HRID 1755928Notes

Reaction equation

HRID 1755928 reaction equation
[CH2:1]([O:3][CH:4]=[C:5]([C:9]([O-:11])=O)[C:6]([O-])=O)[CH3:2].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1([O:25]C2C=CC=CC=2)C=CC=CC=1>>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[N:12][C:13]2[C:18]([C:9]=1[OH:11])=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:25])[CH3:2]

Participants

4

Reactant 3

HCID 6115AnilineHCID 7583Diphenyl EtherHCID 23498110HCID 23498110, compound

Product 1

HCID 178469510HCID 178469510, compound

Procedure

The intermediates (1) are prepared according to the procedures described in J. Amer Chem. Soc. 68, 1204 (1946). Ethoxymethylenemalonate is warmed with an appropriate aniline to give an anil which cyclizes upon heating in boiling diphenylether to give the ethyl-4-hydroxyquinoline-3-carboxylate. Reaction of this intermediate with phosphorus oxychloride gives the intermediate (1). The intermediates (2) are either commercially available or can be prepared from the corresponding ester by hydrolysis. The intermediate (3) can be prepared from (6) by ##STR11## treatment with hydroxylamine hydrochloride followed by reduction of the oxime with nickle/aluminum alloy as described in U.S. Pat. No. 3,875,163, or, when a weaker reducing agent is required, by treatment with ammonium acetate followed by reduction with sodium cyanoborohydride as described in J. Amer. Chem. Soc., 68, 7032 (1979). The intermediate (6) can be prepared. as described in U.S. Pat. No. 4,816,464. The intermediate R8NHR17 where R17 is ##STR12## and R8 is not H can be prepared from (3) by acylation with R15COCl or (R15CO)2O or formylation with formic acetic anhydride followed by reduction with lithium aluminum hydride.

Workup

  1. customto give an anil which
  2. temperatureupon heating

Sources & evidence

ORD record
ord-95c78d62166d42e789f3302b9f026f3b
Source dataset
uspto-grants-1995_08
Patent number
US05438064

Reaction notes

Loading…