Potassium Nitrate → 2-Acetylamino-5-amino-6-nitroindan

HRID 1739804Notes

Reaction equation

HRID 1739804 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[C:6]([NH:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH2:19])[CH:16]=2)[CH2:11]1)(=[O:8])[CH3:7]>OS(O)(=O)=O>[C:6]([NH:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][C:14]([N+:1]([O-:4])=[O:2])=[C:15]([NH2:19])[CH:16]=2)[CH2:11]1)(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 14820513N-(5-amino-2,3-dihydro-1H-inden-2-yl)acetamide

Product 1

HCID 218375442-Acetylamino-5-amino-6-nitroindanYield 79.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

1.62 g of KNO3 is introduced in portions into 2.85 g (15 mmol) of 2-acetylamino-5-aminoindan in 7.5 ml of concentrated H2SO4 that has been cooled to 0° C. The whole is stirred for 3 hours at 0° C. and then poured into ice-cold 6N sodium hydroxide solution, stirred, extracted with methylene chloride and then washed, dried and evaporated. 2.8 g of a black solid are isolated, which is purified on silica (eluant:methylene chloride/methanol: 97/3). In that manner, 1.46 g of the expected product are isolated. Yield: 42%.

Workup

  1. stirringstirred
  2. extractionextracted with methylene chloride
  3. washwashed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-e6a96f7ecf414abe93cddf0d9394bc48
Source dataset
uspto-grants-1999_10
Patent number
US05968954

Reaction notes

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