Nitric Acid → N-(5-nitro-indan-2-yl)-acetamide

HRID 1701344Notes

Reaction equation

HRID 1701344 reaction equation
[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2].[N+:14]([O-])([OH:16])=[O:15]>>[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 12452137N-(2,3-Dihydro-1H-inden-2-yl)acetamide

Product 1

HCID 14820512N-(5-nitro-indan-2-yl)-acetamide

Conditions

Temperature
0 °C

Procedure

18.5 g. of the acetamide (0.105 mole) was added in portions to nitric acid (185 ml.; d=1.51), stirred and maintained below 0° C. The reaction was allowed to warm to 0° C., poured onto crushed ice and extracted with chloroform which was washed with 5% aqueous sodium bicarbonate and evaporated to give crude N-acetyl-5-nitro-2-indanamine which was purified by crystallization from isopropanol, m.p. 143°-144° C.

Workup

  1. temperaturemaintained below 0° C
  2. additionpoured
  3. customonto crushed ice
  4. extractionextracted with chloroform which
  5. washwas washed with 5% aqueous sodium bicarbonate
  6. customevaporated

Sources & evidence

ORD record
ord-37e8f1b38bc04e3f99cb1f16389855b3
Source dataset
uspto-grants-1980_03
Patent number
US04192888

Reaction notes

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