Ethyl Acetate → HCID 14207566, compound

HRID 1252736Notes

Reaction equation

HRID 1252736 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]([CH2:13][CH3:14])[C:5]([C:6](OCC)=[O:7])=[C:4]([NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:3]=1[CH3:21].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O>[NH2:1][C:2]1[CH:12]=[C:11]([CH2:13][CH3:14])[C:5]2[C:6](=[O:7])[O:17][C:16]([O:18][CH2:19][CH3:20])=[N:15][C:4]=2[C:3]=1[CH3:21]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 14207584HCID 14207584, compound

Product 1

HCID 14207566HCID 14207566, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of ethyl 4-amino-2-ethoxycarbonylamino-6-ethyl-3-methyl-benzoate (20 mg) in concentrated sulphuric acid (3 ml) was stirred at room temperature for 4 hrs. The solution was added dropwise to an ice-cold stirred mixture of ethyl acetate and saturated sodium bicarbonate solution. After neutralization, the mixture was extracted with ethyl acetate. The organic extract was dried over magnesium sulphate and evaporated to give a solid. This material is further purified by thick layer chromatography (25% ethyl acetate: pet,. ether 30-60) to yield 7-amino-2-ethoxy-5-ethyl-8-methyl-4H-3,1-benzoxazin-4-one (10 mg). IR (CHCl3): 3500, 3420, 1740, 1650, 1610, 1565 cm-1. H--NMR (CDCl3): 1.20 (t, 3H, CH3), 1.40 (t, 3H, CH3), 2.20 (s, 3H, CH3 --Ar), 3.05 (q, 2H, CH2Ar), 4.50 (q, 2H, CH2O), 6.50 (s, 1H, ArH).

Workup

  1. extractionAfter neutralization, the mixture was extracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over magnesium sulphate
  4. customevaporated
  5. customto give a solid
  6. customThis material is further purified by thick layer chromatography (25% ethyl acetate: pet,. ether 30-60)

Sources & evidence

ORD record
ord-91cc89ac6b174fe3bcdcc67d3ab93f8e
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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