Hydrochloric Acid → HCID 66737937, compound

HRID 1640680Notes

Reaction equation

HRID 1640680 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.B(Cl)(Cl)Cl.[NH2:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#N)=[CH:17][CH:16]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[OH-:28].[Na+]>C1(C)C=CC=CC=1.O>[NH2:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[NH:1][CH2:2][CH2:3]3)=[O:28])=[CH:17][CH:16]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 10328Indoline2×HCID 133964-AminobenzonitrileHCID 14798Sodium HydroxideHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 66737937HCID 66737937, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
70 °C

Procedure

5 g (42 mmol) of indoline are dissolved in 50 ml of toluene. In a separate flask, 70 ml of toluene are cooled to 5° C., and 100 ml of boron trichloride (10% solution in xylene) are added dropwise at this temperature under nitrogen. The indoline is subsequently added dropwise to this solution at 5-10° C., and 5.4 g (46 mmol) of 4-aminobenzonitrile are subsequently added in portions over the course of 30 min. The mixture is stirred at 5-10° for a further 15 min, and 6.7 g (50 mmol) of aluminium chloride are then added in portions at the temperature indicated. The mixture is heated under reflux for 6 h. For work-up, the reaction mixture is cooled to 70° C., and 10 ml of water are added dropwise, during which the temperature rises slightly and the solution becomes cloudy. 60 ml of 2 N hydrochloric acid are subsequently added, during which a clear solution is again formed, and the mixture is warmed under reflux for 12 h. The reaction mixture is poured into ice-water, adjusted to pH=12 using conc. NaOH and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and evaporated, and the residue is chromatographed over a column with ethyl acetate. The combined product fractions are recrystallised from petroleum ether, giving 3.8 g of yellow crystals (4-aminophenyl)-(2,3-dihydro-1H-indol-7-yl)methanone. (M.p. 133-135° C.)

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 6 h
  3. customis again formed
  4. temperaturethe mixture is warmed
  5. temperatureunder reflux for 12 h
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic phases are dried over sodium sulfate
  8. customevaporated
  9. customthe residue is chromatographed over a column with ethyl acetate
  10. customThe combined product fractions are recrystallised from petroleum ether

Sources & evidence

ORD record
ord-504cd7c310824714b3b98e094452fbb9
Source dataset
uspto-grants-2012_02
Patent number
US08114882B2

Reaction notes

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