Nitric Acid → HCID 13835066, compound

HRID 2374480Notes

Reaction equation

HRID 2374480 reaction equation
[CH2:1]([C:3]1([CH2:13][CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12])[CH3:2].[N+:15]([O-])([OH:17])=[O:16]>S(=O)(=O)(O)O>[CH2:13]([C:3]1([CH2:1][CH3:2])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=2)[NH:5][C:4]1=[O:12])[CH3:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 151532213,3-diethyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 13835066HCID 13835066, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 3,3-diethyl-1,3-dihydro-indol-2-one (10.0 g, 52.84 mmol, A. Mertens et al., J. Med. Chem. 1987, 30, 1279-1287) in conc. sulfuric acid (50 ml) was added slowly a mixture of nitric acid (65%, 5.12 g, 3.63 ml, 52.84 mmol) and conc. sulfuric acid (10 ml) at 0° C. After 2 h at room temperature the mixture was poured into ice water. The precipitate was filtered off, washed with water and dried to yield 11.7 g 3,3-diethyl-5-nitro-1,3-dihydro-indol-2-one (49.95 mmol, 94%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-0cb8bf5427564fac9b3b78eae65dc2b8
Source dataset
uspto-grants-2008_12
Patent number
US07462639B2

Reaction notes

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