Aniline → Ethyl 8-methoxy-4-(phenylamino)quinoline-3-carboxylate

HRID 66775

Reaction equation

HRID 66775 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[C:20]1([NH:19][C:2]2[C:11]3[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 3045573-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl ester

Product 1

HCID 1507948Ethyl 8-methoxy-4-(phenylamino)quinoline-3-carboxylateYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6.0 g (22.5 mmoles) of ethyl 4-chloro-8-methoxy-3-quinolinecarboxylate in 80 ml of tetrahydrofuran was added 2.3 g (24.8 mmoles) of aniline in 60 ml of tetrahydrofuran. The solution was briefly warmed and after standing for 10 minutes, a yellow solid began to precipitate. The mixture was kept at room temperature for 18 hours. The solvent was rotary evaporated. The residue dissolved in 200 ml of methanol and the pH made slightly basic (pH 8) with sodium bicarbonate. Water (700 ml) was added and an oil formed which solidified and after standing, additional solid crystallized. The solid was filtered and air-dried to give 6.9 g (95%) of crude material. The solid was dissolved in 300 ml of hot isooctane and the solution was charcoaled and filtered. The volume of the filtrate was reduced to 150 ml. Upon cooling, pale yellow needles separated; 6.5 g (89%); m.p. 120°-121° C.

Workup

  1. temperatureThe solution was briefly warmed
  2. customto precipitate
  3. waitThe mixture was kept at room temperature for 18 hours
  4. dissolutionThe residue dissolved in 200 ml of methanol
  5. additionWater (700 ml) was added
  6. customan oil formed which
  7. customadditional solid crystallized
  8. filtrationThe solid was filtered
  9. customair-dried

Sources & evidence

ORD record
ord-30923a12ae1f4c92948fb4334f7c924e
Source dataset
uspto-grants-1982_08
Patent number
US04343804

Linked notes

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