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

HRID 55536Notes

Reaction equation

HRID 55536 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 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
  2. customas described in Preparation 88
  3. customthe resulting crude product was crystallized by trituration with isopropanol

Sources & evidence

ORD record
ord-8dd020bd625a45edb14beade81259e53
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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