Nitric Acid → HCID 11481739, compound

HRID 1991468Notes

Reaction equation

HRID 1991468 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-a5bc8a3343aa41eaa63ae51472ec0030
Source dataset
uspto-grants-2010_01
Patent number
US07645887B2

Reaction notes

Loading…