Nitric Acid → HCID 11481739, compound

HRID 2424331Notes

Reaction equation

HRID 2424331 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:11][C:12]([NH2:14])=[O:13].[N+:15]([O-])([OH:17])=[O:16].C(#N)C.CO>C(O)(C(F)(F)F)=O>[N+:15]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]([CH2:11][C:12]([NH2:14])=[O:13])[C:2](=[O:1])[CH2:10]2)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 840219HCID 840219, compoundHCID 21959252Acetonitrile methanol

Product 1

HCID 11481739HCID 11481739, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of 2-(2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide 1 (400 mg, 2.1 mmol) in TFA (20 ml) was added fuming nitric acid (170 μl, 2.7 mmol) over 10 minutes. Following addition, the ice bath was removed and the mixture was stirred at room temperature for 5 minutes, then poured carefully into ice water. The precipitate was collected, washed with water until pH 7 and dried to give a crude solid. Cristallization in a mixture acetonitrile/MeOH afforded the 2-(5-nitro-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide 5 as a green-gray solid.

Workup

  1. additionaddition
  2. customthe ice bath was removed
  3. additionpoured carefully into ice water
  4. customThe precipitate was collected
  5. washwashed with water until pH 7
  6. customdried
  7. customto give a crude solid

Sources & evidence

ORD record
ord-225f633487c0446e9197963c19179619
Source dataset
uspto-grants-2011_06
Patent number
US07964593B2

Reaction notes

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