Aniline → HCID 18433003, compound

HRID 2305567Notes

Reaction equation

HRID 2305567 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:10][C:11](=O)[CH2:12][C:13](=O)[CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15]1)C>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH2:23][CH:14]1[C:13]1[NH:1][C:2]2[C:7]([C:11](=[O:10])[CH:12]=1)=[CH:6][CH:5]=[CH:4][CH:3]=2

Participants

5

Reactant 2

HCID 6115AnilineHCID 65405396HCID 65405396, compound

Product 1

HCID 18433003HCID 18433003, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture containing aniline (0.7 ml, 7.7 mmol), p-toluene sulfonic acid (0.037 g,0.19 mmol) and (RS)-3-oxo-3-(1,2,3,4-tetrahydro-naphthalen-2-yl)-propionic acid ethyl ester (1.9 g, 7.7 mmol) in toluene (10 ml) was refluxed for 2.5 hours, and water was removed azeotropically. Reaction mixture was concentrated, diluted with diphenylether (8 ml), refluxed for 45 min., cooled to room temperature and diluted with Et2O (150 ml). The resulting solid was filtered, washed with Et,O and CH2Cl2 to provide (RS)-2-(1,2,3,4-Tetrahydro-naphthalen-2-yl)-1H-quinolin-4-one (0.67 g, 32%) as a light yellow solid, mp.>300° C., MS: m/e=275 (M+).

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. customwater was removed azeotropically
  3. customReaction mixture
  4. concentrationwas concentrated
  5. additiondiluted with diphenylether (8 ml)
  6. temperaturerefluxed for 45 min.
  7. additiondiluted with Et2O (150 ml)
  8. filtrationThe resulting solid was filtered
  9. washwashed with Et,O and CH2Cl2

Sources & evidence

ORD record
ord-6ad63a31955a488e80c600e208a1801a
Source dataset
uspto-grants-2002_08
Patent number
US06440995B1

Reaction notes

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