Nitric Acid → 5-Chloro-6-nitro-1-indanone

HRID 46630

Reaction equation

HRID 46630 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[N+:12]([O-])([OH:14])=[O:13]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:12]([O-:14])=[O:13])[C:7](=[O:11])[CH2:6][CH2:5]2

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 1425995-Chloro-1-indanone

Product 1

HCID 221190235-Chloro-6-nitro-1-indanone

Conditions

Temperature
-20 °C

Procedure

86.0 g (0.51 mole) of 5-chloro-1-indanone are introduced in portions into 540 ml of fuming nitric acid (d=1.54), cooled to -20° C., so that the temperature of the reaction mixture remains between -10° and -15° C. After the addition has ended, the mixture is subsequently stirred for 45 minutes at -15° to -20° C., the reaction solution is poured onto ice and the precipitate which has separated out is filtered off and washed with water. The crude product of melting point 110°-113° is recrystallized from ethanol, whereby the melting point of the pure 5-chloro-6-nitro-1-indanone rises to 126°-128° C.

Workup

  1. customremains between -10° and -15° C
  2. additionAfter the addition
  3. additionthe reaction solution is poured onto ice
  4. customthe precipitate which has separated out
  5. filtrationis filtered off
  6. washwashed with water
  7. customThe crude product of melting point 110°-113° is recrystallized from ethanol, whereby the melting point of the pure 5-chloro-6-nitro-1-indanone
  8. customrises to 126°-128° C.

Sources & evidence

ORD record
ord-d3a6c63b4a5c415e88d600c12938b6bd
Source dataset
uspto-grants-1979_11
Patent number
US04174397

Linked notes

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