4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → HCID 3126580, compound

HRID 2052689Notes

Reaction equation

HRID 2052689 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1>C1(C)C(C)=CC=CC=1>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 10328Indoline

Product 1

HCID 3126580HCID 3126580, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

An initial solution of 22.6 g of 4-chloro-3-nitrobenzotrifluoride and 29.8 g of indoline in 500 ml of xylene is stirred and refluxed under N2 for 18 hours. The indoline HCl salt which separates is filtered off, and the xylene filtrate is washed with water, with 3 N HCl, with 3 N--NaOH, and finally again with water, dried over MgSO4, and concentrated to an oil on a rotovac at 60° C., first at aspirator pressure, then in vacuo. This oil is taken up in 100 ml hexane and allowed to crystallize 18 hours to yield 1-(2-nitro-4-trifluoromethylphenyl)indoline, m.p. 89°-92° C.

Workup

  1. temperaturerefluxed under N2 for 18 hours
  2. filtrationThe indoline HCl salt which separates is filtered off
  3. washthe xylene filtrate is washed with water, with 3 N HCl, with 3 N
  4. dry with materialNaOH, and finally again with water, dried over MgSO4
  5. concentrationconcentrated to an oil on a rotovac at 60° C., first at aspirator pressure
  6. customto crystallize 18 hours

Sources & evidence

ORD record
ord-e2336098f7604134873f0982e6945a18
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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