Indoline → 1-(2-Nitrophenyl)indoline

HRID 2052687Notes

Reaction equation

HRID 2052687 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]>>[N+:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 10328IndolineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 74105181-(2-Nitrophenyl)indoline

Conditions

Temperature
120 °C

Procedure

11.0 g (0.10 mole) of indoline and 28.2 g of 1-fluoro-2-nitrobenzene are combined and the resultant solution is stirred and heated to 120° C. and kept at that temperature 18 hours. The reaction mixture is then cooled to room temperature and partitioned between chloroform and water. The chloroform layer is separated, washed with water, dried and concentrated in vacuum. The residue is dissolved in isopropylether from which 1-(2-nitrophenyl)indoline, m.p. 62°-64° C., precipitates on standing.

Workup

  1. customkept at that temperature 18 hours
  2. temperatureThe reaction mixture is then cooled to room temperature
  3. custompartitioned between chloroform and water
  4. customThe chloroform layer is separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated in vacuum
  8. dissolutionThe residue is dissolved in isopropylether from which 1-(2-nitrophenyl)indoline, m.p. 62°-64° C.
  9. customprecipitates

Sources & evidence

ORD record
ord-7f61eed643c049daa497e4313c3a42d2
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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