Nitric Acid → 3-(4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

HRID 1265351Notes

Reaction equation

HRID 1265351 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[NH:11][C:10]2=[O:20])=[C:4]([F:21])[CH:3]=1.[N+:22]([O-])([OH:24])=[O:23]>>[Cl:1][C:2]1[CH:3]=[C:4]([F:21])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[NH:11][C:10]2=[O:20])=[C:6]([N+:22]([O-:24])=[O:23])[C:7]=1[OH:8]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 177702713-(4-chloro-2-fluoro-5-hydroxyphenyl)6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 569772053-(4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Procedure

3-(4-chloro-2-fluoro-5-hydroxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (2.5 g) was added to an ice cooled con. nitric acid (50 ml). After stirring for 1 hr, the reaction mixture was poured into ice-cold water. The yellow crystals were collected by filtration to afford the title compound (0.9 g). The filtrate was extracted by ethyl acetate (200 ml) and washed with brine. The organic phase was dried over anhydrous sodium sulfate. After removal of the solvent, 0.6 g of title compound was obtained as yellow crystal.

Workup

  1. temperaturecooled con
  2. additionthe reaction mixture was poured into ice-cold water
  3. filtrationThe yellow crystals were collected by filtration

Sources & evidence

ORD record
ord-e488e705e4b34992a0e3d56592909282
Source dataset
uspto-grants-2003_04
Patent number
US06545161B2

Reaction notes

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