1,2-Dichloroethane → HCID 86701074, compound

HRID 589482Notes

Reaction equation

HRID 589482 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9]C=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[CH2:15]([NH2:17])[CH3:16].C(Cl)CCl.CC[N:24](C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[NH2:1][C:2]1[C:3]([C:4]([NH:17][CH2:15][CH3:16])=[O:6])=[CH:7][N:24]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 2196332-Amino-3-nitrobenzoic acid

Product 1

HCID 86701074HCID 86701074, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-3-nitrobenzoic acid (CXXVI) (366 mg, 2.0 mmol) in DCM (5 mL) and DMF (1 mL) was added ethylamine hydrochloride and EDC. The mixture was cooled to 0° C. under argon before added DIPEA. The reaction was stirred at room temperature for 3 h. The solution was concentrated under vacuum, dissolved in water and extracted with EtOAc. The combined organic phases were washed with brine, dried over MgSO4 and concentrated under vacuum. The residue was purified on a silica gel column (100% CHCl3→5:95 MeOH[7N NH3]:CHCl3) to give 4-amino-N-ethyl-5-nitronicotinamide (CXXVII) as a yellow solid (200 mg, 0.95 mmol, 47.6% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 1.14 (t, J=7 Hz, 3H), 3.28 (q, J=6 Hz, 2H), 8.97 (s, 1H), 9.06 (s, 1H).

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. dissolutiondissolved in water
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified on a silica gel column (100% CHCl3→5:95 MeOH[7N NH3]:CHCl3)

Sources & evidence

ORD record
ord-a753d939585e462baeca96df985f9e02
Source dataset
uspto-grants-2016_01
Patent number
US09233104B2

Reaction notes

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