Cyclohexylamine → HCID 23378471, compound

HRID 2117028Notes

Reaction equation

HRID 2117028 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-6c95606ea09f4465a8306497b164b10d
Source dataset
uspto-grants-2008_10
Patent number
US07439258B2

Reaction notes

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