2,5-Dichloronitrobenzene → HCID 20379503, compound

HRID 2051681Notes

Reaction equation

HRID 2051681 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)[NH2:3].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[ClH:10].[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([NH:3][CH:2]([CH3:1])[C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1

Participants

5

Reactant 3

HCID 69772,5-DichloronitrobenzeneHCID 10340Sodium CarbonateHCID 27716881-(Pyridin-3-yl)ethan-1-amine

Product 1

HCID 20379503HCID 20379503, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 52.5 parts of α-methyl-3-pyridinemethanamine, 84.5 parts of 1,4-dichloro-2-nitrobenzene, 53 parts of sodium carbonate and 320 parts of 1-butanol is stirred and refluxed for 72 hours. The reaction mixture is evaporated and water is added to the residue. The oily product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2,2'-oxybispropane, 4-methyl-2-pentanone and 2-propanol. The oily salt is separated and crystallized from 2-propanol, yielding 46 parts (34%) of N-(4-chloro-2-nitrophenyl)-α-methyl-3-pyridinemethanamine monohydrochloride.

Workup

  1. temperaturerefluxed for 72 hours
  2. customThe reaction mixture is evaporated
  3. additionwater is added to the residue
  4. extractionThe oily product is extracted with methylbenzene
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe oily salt is separated
  9. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-f457a9b11d9742c7b4b96ef3b3272206
Source dataset
uspto-grants-1980_01
Patent number
US04181802

Reaction notes

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