Water → N-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]benzamide

HRID 2052696Notes

Reaction equation

HRID 2052696 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1.C(N(CC)CC)C.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>C(Cl)Cl>[C:25]([NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 125191192-(2,3-dihydro-1H-indol-1-yl)aniline hydrochloride

Product 1

HCID 12519128N-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred mixture, under N2, of 24.6 g of 1-(2-aminophenyl)indoline hydrochloride in 225 ml of dry CH2Cl2 is treated with 20.2 g of triethylamine over 10 minutes. The mixture is cooled to 0°-5° C., and kept at that temperature while a solution of 14.1 g of benzoyl chloride and 25 ml of CH2Cl2 is added dropwise over 1.0 hour. After stirring at room temperature overnight, H2O was added and the layers are separated. The organic phase is washed further with H2O, 3 N--HCl, 3 N--NaOH, again with H2O, and dried. The solvent is removed to leave an oil which crystallizes on standing to yield 1-(2-benzamidophenyl)indoline, m.p. 73°-76° C.

Workup

  1. temperatureThe mixture is cooled to 0°-5° C.
  2. additionis added dropwise over 1.0 hour
  3. customthe layers are separated
  4. washThe organic phase is washed further with H2O, 3 N
  5. dry with materialHCl, 3 N--NaOH, again with H2O, and dried
  6. customThe solvent is removed
  7. customto leave an oil which
  8. customcrystallizes

Sources & evidence

ORD record
ord-cac03fc7abc6430dbe39728ecf6aa039
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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