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

HRID 1738272Notes

Reaction equation

HRID 1738272 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-4e1490aa85514ddbb996c22e1b784f30
Source dataset
uspto-grants-1999_10
Patent number
US05962470

Reaction notes

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