Isopropanol → 6-Isopropoxy-2-methylamino-3-nitropyridine

HRID 1601869Notes

Reaction equation

HRID 1601869 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+].[CH:15]([OH:18])([CH3:17])[CH3:16]>CN(C)C=O>[CH:15]([O:18][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1)([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 107500946-chloro-N-methyl-3-nitropyridin-2-amine

Product 1

HCID 108461726-Isopropoxy-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), 2.7 ml of isopropanol 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 6.10 g of the title compound, melting at 75-76° 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-c819eb3696cd4f3d87a10a410174094a
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

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