Aniline → 2-(Phenylamino)quinoline-8-carboxylic acid

HRID 1056008

Reaction equation

HRID 1056008 reaction equation
[H-].[Na+].Cl[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[C:7]([C:14]([OH:16])=[O:15])[CH:8]=[CH:9][CH:10]=2)[N:5]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1.CCOCC>[C:18]1([NH:17][C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[C:7]([C:14]([OH:16])=[O:15])[CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 24758Sodium hydrideHCID 190262012-Chloroquinoline-8-carboxylic acid

Product 1

HCID 897820232-(Phenylamino)quinoline-8-carboxylic acidYield 35%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

NaH (60% w/w in mineral oil; 0.549 g, 13.73 mmol) was added to a mixture of 2-chloroquinoline-8-carboxylic acid (181a, 0.95 g, 4.58 mmol) and aniline (0.834 ml, 9.15 mmol) in THF (11 ml) at 0° C.; the reaction was heated to 50° C. for 2 h. The mixture was diluted with 75 ml of Et2O and washed with 1 N NaOH. The organic layer was separated, and the aq. layer was acidified to ˜pH 1 with 5 N HCl and extracted 4 times with 75 ml of EtOAc. All organic extracts were then combined dried over Na2SO4, and concentrated to give 2-(phenylamino)quinoline-8-carboxylic acid (35% yield) as a light-brown solid. MS (ESI, pos. ion) m/z: 265.2 (M+1).

Workup

  1. washwashed with 1 N NaOH
  2. customThe organic layer was separated
  3. extractionextracted 4 times with 75 ml of EtOAc
  4. dry with materialAll organic extracts were then combined dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c3d25280e6ad4f8382b91b7634928dcd
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Linked notes

Loading…