Ammonium Hydroxide → 2-Amino-6-chloro-N-methoxy-N-methyl-nicotinamide

HRID 30097Notes

Reaction equation

HRID 30097 reaction equation
Cl[C:2]1[N:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5].[OH-].[NH4+:16]>O1CCCC1>[NH2:16][C:2]1[N:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 534034112,6-Dichloro-N-methoxy-N-methylpyridine-3-carboxamide

Product 1

HCID 585908242-Amino-6-chloro-N-methoxy-N-methyl-nicotinamideYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,6-Dichloro-N-methoxy-N-methyl-nicotinamide (202.4 mg, 0.8610 mmol, Example 1) and concentrated ammonium hydroxide (1.8 mL, 29.4%, Fisher) in tetrahydrofuran (2.5 mL) were heated to 155° C. in the microwave for 2 hr. The reaction mixture was concentrated and the residue was purified on silica gel with hexanes/ethyl acetate to give 2-Amino-6-chloro-N-methoxy-N-methyl-nicotinamide (14.3 mg, 8% yield). HRMS, observed: 215.0463, Calcd for M+: 215.0462.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified on silica gel with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-2252cf8254b348ab8f83890ebf6412be
Source dataset
uspto-grants-2008_09
Patent number
US07423051B2

Reaction notes

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