Water → N-[(4-chlorophenyl)methyl]-3-nitropyridin-2-amine

HRID 653663Notes

Reaction equation

HRID 653663 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=1.CC1C=CC(CC)=CN=1.O>C1(C)C(C)=CC=CC=1.C(O)(=O)C>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH:17][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 77285-Ethyl-2-methylpyridineHCID 660364-ChlorobenzylamineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 2800352N-[(4-chlorophenyl)methyl]-3-nitropyridin-2-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7237O-XyleneSolvent

Procedure

A solution of 26.5 g of 2-chloro-3-nitropyridine, 23.7 g of 4-chlorobenzylamine and 25 ml of 2-methyl-5-ethylpyridine in 200 ml of xylene is refluxed for 12 hours. The reaction mixture is then cooled, water and acetic acid are added and the resulting mixture is then extracted with ether. The organic phase is dried over magnesium sulfate, filtered and then evaporated under vacuum to give an oil which crystallizes from isopropyl ether. The crystals are filtered off and then dried to give 27 of 2-(4-chlorophenylmethylamino)-3-nitropyridine in the form of crystals melting at 100° C.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. extractionthe resulting mixture is then extracted with ether
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customto give an oil which
  7. customcrystallizes from isopropyl ether
  8. filtrationThe crystals are filtered off
  9. customdried

Sources & evidence

ORD record
ord-5518fbe4c217475c895a8a108ff87527
Source dataset
uspto-grants-1992_07
Patent number
US05128359

Reaction notes

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