Sulfuric Acid → 7-Isopropylindoline-2,3-dione

HRID 2249561Notes

Reaction equation

HRID 2249561 reaction equation
[OH:1]S(O)(=O)=O.ON=[CH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]([CH3:20])[CH3:19])=[O:10]>O>[CH:18]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[NH:11][C:9](=[O:10])[C:8]2=[O:1])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 714439472-(Hydroxyimino)-N-[2-(propan-2-yl)phenyl]acetamide

Product 1

HCID 122727937-Isopropylindoline-2,3-dioneYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of concentrated H2SO4 (210 ml) and H2O (50 ml), was added over 20 min (26.7 g, 0.13 mol) of 2-(hydroxyimino)-N-(2-isopropylphenyl)acetamide. The mixture was stirred at 75° C. for 2 hr, cooled and poured onto cracked ice. After standing for 15 min, it was extracted with EtOAc, washed with water, dried over MgSO4, and concentrated. Air drying afforded (23.8 g, 97%) of crude product). 1H NMR (300 MHz, CDCl3) δ 8.15 (b, NH), 7.49 (d, 2H), 7.11 (t, 1H), 2.87(m, 1H), 1.30 (d, 6H); ESI (+) MS m/e=190 (MH+), ESI (−) MS m/e=188 (MH−).

Workup

  1. temperaturecooled
  2. additionpoured
  3. waitAfter standing for 15 min
  4. extractionit was extracted with EtOAc
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customAir drying

Sources & evidence

ORD record
ord-ba45429c5c6e48a8ae8583444ef12e6b
Source dataset
uspto-grants-2008_01
Patent number
US07314886B2

Reaction notes

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