Cyclohexylamine → HCID 23378471, compound

HRID 1280104Notes

Reaction equation

HRID 1280104 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](OC)=[C:7]([N+:13]([O-:15])=[O:14])[N:6]=1)=[O:4].[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:22][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:7]([N+:13]([O-:15])=[O:14])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 23378472Methyl 5-methoxy-6-nitropyridine-2-carboxylate

Product 1

HCID 23378471HCID 23378471, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-methoxy-6-nitro-pyridine-2-carboxylic acid methyl ester (0.585 g, 2.75 mmol) and cyclohexylamine (0.636 mL, 5.51 mmol) in DMF (8 mL) was heated at 70° C. for 20 h. The mixture was poured on brine (50 mL) while mixing vigorously. The solid formed was filtered, washed with water and then dissolved in EtOAc. The solution was washed with water, saturated NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated to give 5-cyclohexylamino-6-nitro-pyridine-2-carboxylic acid methyl ester as a brown oil (0.558 g) which was used in the subsequent step without purification.

Workup

  1. additionThe mixture was poured on brine (50 mL)
  2. additionwhile mixing vigorously
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with water
  6. dissolutiondissolved in EtOAc
  7. washThe solution was washed with water, saturated NaHCO3 and brine
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-90d48d5a4d484eba87f917d25e5b71e6
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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