Aniline → HCID 178469510, compound

HRID 1287619Notes

Reaction equation

HRID 1287619 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:10][CH:11]=[C:12]([C:18](OCC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])C.C1(OC2C=CC=CC=2)C=CC=CC=1.C1(C2C=CC=CC=2)C=CC=CC=1>>[OH:10][C:11]1[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:1]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 4

HCID 6115AnilineHCID 6871Diethyl (ethoxymethylene)malonateHCID 7095BiphenylHCID 7583Diphenyl Ether2×

Product 1

HCID 178469510HCID 178469510, compound

Procedure

In step 1 of sequence A, an aniline, substituted by the appropriate R2 group or groups, is condensed with a dialkyl alkoxymethylenemalonate such as diethyl ethoxymethylenemalonate by heating at 120° to 150° C. The intermediate formed is condensed by heating at a temperature of 150° to 300° C. in a high boiling inert solvent such as diphenyl ether or mixtures of diphenyl ether and biphenyl (e.g. Dowtherm A) to give the ethyl 4-hydroxyquinoline-3-carboxylate product of step 1.

Workup

  1. temperatureby heating at 120° to 150° C
  2. customThe intermediate formed
  3. customcondensed

Sources & evidence

ORD record
ord-529545dc62f143edb2c8a378e4a4b408
Source dataset
uspto-grants-1976_10
Patent number
US03985753

Reaction notes

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