HCID 22450431, compound → Methyl(2-pyridylmethyl)amine

HRID 1585035Notes

Reaction equation

HRID 1585035 reaction equation
CSC(=NC)[N:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10](Cl)=[CH:9]C=1)[CH3:5].C[NH:17]C(N(C)CC1C=CN=CC=1)=S>[N+](C)([O-])=O>[CH3:5][NH:4][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:17]=1

Participants

4

Reactant 2

HCID 22450431HCID 22450431, compoundHCID 22450450HCID 22450450, compound

Product 1

HCID 88757Methyl(2-pyridylmethyl)amine

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To 4.98 g (0.0205 mole) of S-methyl-N-(4-chloro-benzyl)-N-methyl-N'-methylisothiourea prepared in (1) was added 25 ml of nitromethane and the mixture was reflexed for 6.5 hours. The nitromethane was distilled off and the residue was subjected to silica gel (240 g) column chromatography using MeOH-CHCl3 (1:10) as an eluent to give 5.23 g of an orange-colored oil. To this oil were added small amounts of EtOH and ether and the mixture was cooled in a dry ice-acetone bath and triturated to give crystals. After addition of ether, the crystals were collected by filtration, washed with ether and dried. The procedure gave 3.69 g of the title compound-as pale yellow crystals.

Workup

  1. distillationThe nitromethane was distilled off

Sources & evidence

ORD record
ord-2729e782010441ff9c0e3375d4b634f1
Source dataset
uspto-grants-1999_08
Patent number
US05935981

Reaction notes

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