Ethyl Acetate → HCID 68641301, compound

HRID 1498901Notes

Reaction equation

HRID 1498901 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH:13][CH2:14][CH3:15])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[N:16]([O-])=O.[Na+].O.N.C(OCC)(=O)C>C(O)(=O)C>[CH2:14]([N:13]1[C:12]2[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=2[N:1]=[N:16]1)[CH3:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 2305224ethyl 3-amino-4-(ethylamino)benzoateHCID 12896473Azane;hydrateHCID 23668193Sodium Nitrite

Product 1

HCID 68641301HCID 68641301, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 3-amino-4-ethylaminobenzoate (1.80 g, 9.27 mmol) prepared in the same manner as in the Step 1-1-3 was dissolved in acetic acid (5 ml), and under an ice cooling sodium nitrite (1.28 g, 18.5 mmol) was added to the solution little by little. The mixture was stirred for 10 minutes under a water cooling. The mixture was cooled by ice again and neutralized with a 25% ammonia water. Thereafter, ethyl acetate was added to the mixture, and the resulting mixture was washed with a saturated saline solution and water in order. The washed mixture was dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1 to 1:1) to give the title compound (1.40 g, 69%) as a brown powder.

Workup

  1. additionwas added to the solution little by little
  2. temperatureThe mixture was cooled by ice again
  3. washthe resulting mixture was washed with a saturated saline solution and water in order
  4. dry with materialThe washed mixture was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-41ec76ae24fa4355b68c3bab78f47792
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

Loading…