Benzyl Alcohol → N-Methyl-3-nitro-6-(phenylmethoxy)-2-pyridinamine

HRID 55532Notes

Reaction equation

HRID 55532 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH2:15]([O:22][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 107500946-chloro-N-methyl-3-nitropyridin-2-amine

Product 1

HCID 10491498N-Methyl-3-nitro-6-(phenylmethoxy)-2-pyridinamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 88 was repeated, except that 7.00 g of 6-chloro-2-methylamino-3-nitropyridine (prepared as described in Preparation 66), 1.79 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 4.3 ml of benzyl alcohol and 150 ml of dimethylformamide were used. After working up the product as described in Preparation 88, the resulting crude product was crystallized by trituration with isopropanol, to give 9.02 g of the title compound, melting at 149° C.

Workup

  1. customA procedure similar to that described in Preparation 88
  2. customas described in Preparation 88
  3. customthe resulting crude product was crystallized by trituration with isopropanol

Sources & evidence

ORD record
ord-5cbf7eaf39d44e9289f4b7cbd33afeee
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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