Butyl 2-[2-nitro-4-(trifluoromethyl)phenoxy]propanoate → HCID 18942145, compound

HRID 355356Notes

Reaction equation

HRID 355356 reaction equation
[N+:1]([C:4]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:5]=1[O:6][CH:7]([CH3:15])[C:8](OCCCC)=[O:9])([O-])=O>C(O)(=O)C.[Fe]>[CH3:15][CH:7]1[C:8](=[O:9])[NH:1][C:4]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:5]=2[O:6]1

Participants

4

Reactant 1

HCID 18942139Butyl 2-[2-nitro-4-(trifluoromethyl)phenoxy]propanoate

Product 1

HCID 18942145HCID 18942145, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of butyl 2-(2-nitro-4-trifluoromethylphenoxy)propionate (12.0 g) and iron powder (5 g) in acetic acid (100 ml) was heated to reflux for 1.5 hours. After cooling the reaction mixture was quenched with water and the 2-methyl-6-trifluoromethyl-benzo[1,4]oxazin-3-one (4.49 g, 54% yield) as a grey solid was filtered off and dried mp 142°-4° C.; 1 H NMR (270 Mz): 1.61(3H,d), 4.76(1H,q), 6.7-7.4(2H,m), 8.89(1H,brs) ppm.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureAfter cooling the reaction mixture
  4. customwas quenched with water

Sources & evidence

ORD record
ord-706cdb7fd439474fa14c7e4eb6dba3a7
Source dataset
uspto-grants-1998_11
Patent number
US05830890

Reaction notes

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