Ethyl 2-aminobenzoate → HCID 18432987, compound

HRID 2305566Notes

Reaction equation

HRID 2305566 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH2:8][CH2:7]2)(=O)[CH3:2].C([O:15][C:16](=O)[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH2:19])C.[Al+3].[Cl-].[Cl-].[Cl-].CCCCCC>C1(OC2C=CC=CC=2)C=CC=CC=1.CO>[CH2:9]1[C:10]2[C:6](=[CH:5][C:4]([C:1]3[NH:19][C:18]4[C:17]([C:16](=[O:15])[CH:2]=3)=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:12][CH:11]=2)[CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 6877Ethyl 2-aminobenzoateHCID 8058HexaneHCID 2339761-(2,3-Dihydro-1H-inden-5-yl)ethan-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18432987HCID 18432987, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
200 °C

Procedure

To a mixture of 5-acetylindane (3.0 g, 18.7 mmol) and anthranilic acid ethyl ester (2.8 ml, 18.7 mmol) in diphenylether (47 g) was added portionwise AlCl3 (3.5 g, 26.2 mmol). The reaction mixture was stirred at 200° C. for 2.5 hours and cooled to room temperature. Hexane (100 ml) and MeOH (3 ml) were then added. The so obtained solid was filtered, washed with hexane and stirred in the presence of 5N HCl (85 ml) and acetone (10 ml). After filtration, the solid was again washed with H2O, and stirred with MeOH (15 ml) for 30 min. Filtration provided 2-indan-5-yl-1 H-quinolin-4-one (4.35 g, 89%) as a light yellow solid, MS: m/e=261 (M+).

Workup

  1. temperaturecooled to room temperature
  2. customThe so obtained solid
  3. filtrationwas filtered
  4. washwashed with hexane
  5. stirringstirred in the presence of 5N HCl (85 ml) and acetone (10 ml)
  6. filtrationAfter filtration
  7. washthe solid was again washed with H2O
  8. stirringstirred with MeOH (15 ml) for 30 min
  9. filtrationFiltration

Sources & evidence

ORD record
ord-a1b384a5fdea42dbb553108b8e08fd25
Source dataset
uspto-grants-2002_08
Patent number
US06440995B1

Reaction notes

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