Water → 1-[2-(2-Fluorobenzamido)phenyl]indoline

HRID 2052697Notes

Reaction equation

HRID 2052697 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.[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29].O>C(Cl)Cl>[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28]([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:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 98082-Fluorobenzoyl chlorideHCID 125191192-(2,3-dihydro-1H-indol-1-yl)aniline hydrochloride

Product 1

HCID 203763311-[2-(2-Fluorobenzamido)phenyl]indoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred mixture, under N2, of 9.86 g of 1-(2-aminophenyl)indoline hydrochloride and 100 ml of dry methylene chloride is treated with 8.09 g of triethylamine. The mixture is cooled to 0°-5° C., and a solution of 6.34 g of o-fluorobenzoyl chloride in 25 ml of CH2Cl2 is added over 1 hour at such a rate as to keep the temperature below 5° C. The mixture is then stirred overnight at ambient temperature. Water is added, the organic layer is separated, washed with 3 N--HCl, with 3 N--NaOH, with H2O, dried and concentrated to a crystalline solid of 1-[2-(2-fluorobenzamido)phenyl]indoline, m.p. 139°-141° C.

Workup

  1. temperatureThe mixture is cooled to 0°-5° C.
  2. customthe temperature below 5° C
  3. customthe organic layer is separated
  4. washwashed with 3 N
  5. dry with materialHCl, with 3 N--NaOH, with H2O, dried
  6. concentrationconcentrated to a crystalline solid of 1-[2-(2-fluorobenzamido)phenyl]indoline, m.p. 139°-141° C.

Sources & evidence

ORD record
ord-8acedc1864824e82b8cdfa1988a3e779
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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