4-Chloro-3-nitrobenzophenone → {4-[Methyl(octyl)amino]-3-nitrophenyl}(phenyl)methanone

HRID 1283387Notes

Reaction equation

HRID 1283387 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1Cl)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])([O-:3])=[O:2].[CH3:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N:20]([CH3:19])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 417434-Chloro-3-nitrobenzophenoneHCID 75538Octylmethylamine

Product 1

HCID 23342777{4-[Methyl(octyl)amino]-3-nitrophenyl}(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 9.25 g. of 3-nitro-4-chloro-benzophenone, 10 ml. of ethanol and 10.3 g. of N-methyl-N-octylamine is stirred at 80° to 85 °C for 30 minutes, and then the mixture is poured onto 100 ml. of ice water. The aqueous phase is extracted with 2×75 ml. of benzene. The benzene phases are combined, washed with distilled water until chloride-free, dried over anhydrous magnesium sulphate, filtered, and evaporated in vacuo. 11.57 g. of 3-nitro-4-(N-methyl-N-octylamino)-benzophenone are obtained in the form of an oily residue. On the basis of thin layer chromatographical examination, a pure, uniform product is obtained.

Workup

  1. additionA mixture of 9.25 g
  2. additionthe mixture is poured onto 100 ml
  3. extractionThe aqueous phase is extracted with 2×75 ml
  4. washwashed with distilled water until chloride-free
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f9151830feb14138aa26736c63c0ff39
Source dataset
uspto-grants-1976_08
Patent number
US03975390

Reaction notes

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