Amyl Nitrate → 2-Methyl-2-(4-nitrophenyl)-5-methoxy-6,7-dichloro-1-indanone

HRID 839687Notes

Reaction equation

HRID 839687 reaction equation
[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][C:9]2[C:4](=[C:5]([Cl:14])[C:6]([Cl:13])=[C:7]([O:11][CH3:12])[CH:8]=2)[C:3]1=[O:15].[N+:22]([O-])([O:24]CCCCC)=[O:23]>>[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)[CH2:10][C:9]2[C:4](=[C:5]([Cl:14])[C:6]([Cl:13])=[C:7]([O:11][CH3:12])[CH:8]=2)[C:3]1=[O:15]

Participants

3

Reactant 2

HCID 61250Amyl NitrateHCID 124235872-Methyl-2-phenyl-5-methoxy-6,7-dichloro-1-indanone

Product 1

HCID 203782382-Methyl-2-(4-nitrophenyl)-5-methoxy-6,7-dichloro-1-indanone

Procedure

Amyl nitrate (40 ml.) is added in 10 ml. increments at two hour intervals to 2-methyl-2-phenyl-5-methoxy-6,7-dichloro-1-indanone (9.36 g., 0.03 mole) in polyphosphoric acid (150 g.) at 50°-60° C. with stirring. The total heating period is 8 hours. The reaction mixture is treated with crushed ice-water to precipitate 4.82 g. of 2-methyl-2-(4-nitrophenyl)-5-methoxy-6,7-dichloro-1-indanone which melts at 179°-180° C. after crystallization from butyl chloride.

Workup

  1. temperatureThe total heating period
  2. customto precipitate 4.82 g
  3. customof 2-methyl-2-(4-nitrophenyl)-5-methoxy-6,7-dichloro-1-indanone which melts at 179°-180° C. after crystallization from butyl chloride

Sources & evidence

ORD record
ord-06bffea57ba0466d8e0e85be7b4088c6
Source dataset
uspto-grants-1978_06
Patent number
US04096267

Reaction notes

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