Ethanol → HCID 14207582, compound

HRID 1252725Notes

Reaction equation

HRID 1252725 reaction equation
[CH2:1]([C:3]1[C:4]2[C:8]([C:9]([CH3:15])=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)=[N:7][O:6][CH:5]=2)[CH3:2].C(=O)(O)[O-].[Na+].[CH2:21]([OH:23])[CH3:22]>>[NH2:7][C:8]1[C:9]([CH3:15])=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=[C:3]([CH2:1][CH3:2])[C:4]=1[C:5]([O:23][CH2:21][CH3:22])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 14207581HCID 14207581, compound

Product 1

HCID 14207582HCID 14207582, compoundYield 76%

Procedure

A solution of 4-ethyl-7-methyl-6-nitro-anthranil (300 mg, 0.000146 mol.) in absolute ethanol was mixed with sodium bicarbonate (160 mg, 0.0019 mol.) and was refluxed for 4 hrs. The solution was evaporated to dryness, the residue partitioned between ethyl acetate and 5% hydrochloric acid solution. The organic layer was dried over magnesium sulphate and evaporated to give a solid. This solid was further purified by column chromatography (10% ethyl acetate: pet. ether 30-60) to give ethyl 2-amino-6-ethyl-3-methyl-4-nitro-benzoate as an oil (yield: 276 mg, 76%). IR (neat): 3500, 3400, 2980, 1700, 1620, 1580, 1530 cm-1. H-NMR (CDCl3): 1.20 (t, 3H, CH3), 1.40 (t, 3H, CH3), 2.18 (s, 3H, CH3) 2.78 (q, 3H, CH2), 4.40 (q, 2H, CH2O), 5.05 (br.s, 2H, NH2), 6.91 (s, 1H, ArH).

Workup

  1. temperaturewas refluxed for 4 hrs
  2. customThe solution was evaporated to dryness
  3. customthe residue partitioned between ethyl acetate and 5% hydrochloric acid solution
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. customevaporated
  6. customto give a solid
  7. customThis solid was further purified by column chromatography (10% ethyl acetate: pet. ether 30-60)

Sources & evidence

ORD record
ord-a24e7d2a8a8a43428cf2937506094bb4
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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