Methanol → HCID 59515935, compound

HRID 1161298Notes

Reaction equation

HRID 1161298 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].[C:15]([NH:18][CH2:19][CH2:20][NH2:21])(=[O:17])[CH3:16].CO>>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:21]([CH2:20][CH2:19][NH:18][C:15](=[O:17])[CH3:16])[C:9]2=[O:14])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 66082N-(2-aminoethyl)acetamideHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 59515935HCID 59515935, compound

Procedure

Into a round bottom flask was combined 5-nitro-isochromen-1-one (5.00 g, 0.0235 mol), N-Acetylethylenediamine (7.21 g, 0.0706 mol) and methanol (150 mL, 3.7 mol). The mixture was heated at reflux for 1.5 hours. The mixture was cooled to room temperature and was stirred overnight. LC-MS showed that the starting material was completely consumed. Volatiles were removed and the resulting oil was purified in a methanol:methylene chloride (0-10%) gradient. Fractions containing the desired product, as determined by TLC and LC-MS, were combined and concentrated to produce a yellow solid.

Workup

  1. customInto a round bottom flask was combined
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 1.5 hours
  4. customwas completely consumed
  5. customVolatiles were removed
  6. customthe resulting oil was purified in a methanol
  7. additionFractions containing the desired product
  8. concentrationconcentrated
  9. customto produce a yellow solid

Sources & evidence

ORD record
ord-24105e94f6a44d53a81e144fc4dd76cb
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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