Ethanol → 6-Ethoxy-2-methylamino-3-nitropyridine

HRID 1601865Notes

Reaction equation

HRID 1601865 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:17])[CH3:16]>CN(C)C=O>[CH2:15]([O:17][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1)[CH3:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 107500946-chloro-N-methyl-3-nitropyridin-2-amine

Product 1

HCID 106317836-Ethoxy-2-methylamino-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 88 was repeated, except that 6.00 g of 6-chloro-2-methylamino-3-nitropyridine (prepared as described in Preparation 66), 1.54 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 2.1 ml of ethanol 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 ethanol, to give 5.10 g of the title compound, melting at 101° 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 ethanol

Sources & evidence

ORD record
ord-7e36ac2279884550ba56b685d2d206fd
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

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