Chloroform → HCID 12519117, compound

HRID 2052688Notes

Reaction equation

HRID 2052688 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH2:16][CH2:15]2.C(Cl)(Cl)Cl>O>[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[CH2:16][CH2:15]2

Participants

5

Reactant 3

HCID 6212ChloroformHCID 738951-Fluoro-2-nitrobenzeneHCID 1175965-Chloroindoline

Product 1

HCID 12519117HCID 12519117, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 32.3 g of 1-fluoro-2-nitrobenzene and 92.2 g of 5-chloroindoline are stirred at 120° C. under N2 overnight (20 hours). The mixture is cooled, and stirred vigorously in a two phase chloroform and water system. The undissolved material is filtered off and the organic phase is then separated, washed with 3 N--HCl, water, dried over Na2SO4, and concentrated to an oil which is dried further in vacuo at 90° C. This is taken up in isopropyl ether and refrigerated overnight to provide 5-chloro-1-(2-nitrophenyl)indoline, m.p. 85°-89° C.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationThe undissolved material is filtered off
  3. customthe organic phase is then separated
  4. washwashed with 3 N
  5. dry with materialHCl, water, dried over Na2SO4
  6. concentrationconcentrated to an oil which
  7. customis dried further in vacuo at 90° C

Sources & evidence

ORD record
ord-e33a1fd1db5d49a888ecd10fea7be63f
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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